We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Ashland Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $202 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Ashland are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 115 Rentals in Ashland
    Sort by:
    Default
    Oak Street Cottages ~ Sherwin ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 12
    (6)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4BR Ashland Lodge Style House w/Patio!1 / 31
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Private and Luxurious Cottage Constructed in 2015 with High End Amenities1 / 26
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Mountain Views
    • Secure Parking
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 24, 2015
    Beautiful spot, wonderful cottage, perfect for the four of us. Less than a 5 minute drive to down town Ashland with it's fabulous plays, restaurants and shopping. Lovely new...
    Reviewed May 6, 2015
    Abigail's has new owners, who we found to be friendly and helpful. Super clean cottage, walked to plays two times a day. Great time
    See all reviews
    About this property
    Abigail's Cottage within walking distance to the city center, is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes. Comfortable two bedroom 1 1/2 bath cottage, completely renovated...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Private Suite Near Shakespeare1 / 17
    (19)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    BOOK 2 NIGHTS GET 1 FREE! Art & Garden Cottage ~ Five Minutes From Downtown1 / 11
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Satellite TV
    • Housekeeping Included
    • Internet Access
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Garden Cottage close to Downtown Ashland1 / 6
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520 2650
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    BOOK 2 NIGHTS-GET 1 FREE! Cabin On Hyatt Lake ~ Sleeps Six ~ New Hot Tub! (#44)1 / 22
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Parking
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Central Heating
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Cozy & Private Studio Cottage in Garden Sanctuary + Walk to Downtown Plaza1 / 23
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Parking
    • Terrace
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Ashland Summer Vacation Rental - August 20181 / 13
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Patio
    • Sauna
    • Washer
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Singing Birds Cabin1 / 15
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Parking
    • Grill
    • Porch
    • Central Heating
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2017
    My husband and I had the best vacation at this cozy log cabin.The location was perfect.The view from the porch was just wonderful.Every morning of our week there we enjoyed our...
    Reviewed July 25, 2016
    We had a great time at the Singing Birds. The weather was perfect, which helped, and we enjoyed the seclusion of the location along with the comfort of the rustic cabin. Kind...
    See all reviews
    About this property
    Beautiful log cabin in the Southern Oregon Cascade Mountains. Located very privately on 160 acres of mountain meadowland. Cabin sleeps up to 6 people, but the only door is on the downstairs bath with sleeping beds in the open loft and also downstairs. Full kitchen, full bath down and half bath...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    The Cottage at Grizzly Peak Winery - Sleeps 41 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 2017
    What a sweet location, parklike grounds, vineyard, winery and wonderful welcoming hosts. Virginia & Al made us feel right at home. The cottage is clean, comfortable and...
    See all reviews
    About this property
    Enjoy a free bottle of wine... let us know, red or white... and free admission to one of our summertime concerts (if it coincides with your stay). Nestled on the slopes of Grizzly Peak, less than ten minutes from Downtown Ashland sits our second floor studio cottage! A 600sqft+ studio cottage...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn is NOW OPEN! Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and feature Local Artist Kay...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Private Yard
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 2 blocks to Downtown Ashland Plaza... and 1 block from OSF make this a perfect getaway! This two-story home has three bedrooms; the master has a king-size bed and the guest rooms each have queen-sized beds. There is a spacious living room with plenty of seating and a sofa-bed. The home can...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    2nd Street Cottages, GARDEN SUITE1 / 11
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Terrace
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 31, 2017
    My wife and I stayed in the small apartment on the second floor for a few nights. Sugar met us when we arrived and made the whole transaction very simple for us. The room was...
    Reviewed June 22, 2016
    Lovely cottage with tons of character located in downtown Ashland. We walked just a couple of short blocks to the theater and restaurants. Ours was a spacious, upstairs room...
    See all reviews
    About this property
    THE GARDEN SUITE IS A CHARMING TWO BEDROOM, 2 FULL BATH COTTAGE THAT COMFORTABLY WELCOMES 5 GUESTS. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail and has...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Patio
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note: '1900' Guest House (Next Door) May Also Be Available: (It features a King Bed and Full Kitchen and Bathroom) The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home features...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Romeo1 / 12
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Yard
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We enjoyed our stay. Dermot is charming, and the location is very convenient walking distance to downtown. Our friends rented the Juliet cottage next door, and it was nice to...
    Reviewed August 8, 2015
    We have been staying at this property once a year for over 10 years, and we can hardly wait to return the next year. This rental and it's adjacent cottage are beautifully...
    See all reviews
    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Juliet1 / 15
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Yard
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2017
    The accommodations were well equipped. The beds were very comfortable and we enjoyed sitting on the patio in the mornings and reading or drawing.
    Reviewed July 23, 2014
    I took my 86 year old mother with me to visit Ashland. The cottage was very clean and cozy and my mom was delighted. There is no real living or dining space inside but the...
    See all reviews
    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Perfect vacation cottage1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2016
    Perfectly furnished for our party of four adults; perfectly stocked kitchen; perfect front yard for dining al fresco and watching deer go by; perfect neighborhood for daily...
    Reviewed August 24, 2015
    Great location for walking to theatres as well as restaurantsand shopping in Ashland. Great space for two couples tobe separate or to be together. Front porch is a...
    See all reviews
    About this property
    Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Parking
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Hyatt Lake Cabin Home! 1.5 acres and close access to the lake. Just 5 minutes from the Hyatt Lake Resort, the Pacific Crest Trail and the Table Mountain Winter Play Area!...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Terrace
    • Balcony
    • Grill
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Tower Townhouse is one of the closest properties to the famed Oregon Shakespeare Festival, and just one and half blocks to the entry of the Theaters. The home features a full kitchen, a...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn (scheduled for completion in Spring 2017) Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Parking
    • Mountain Views
    • Patio
    • Balcony
    • Wi-Fi
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully nestled into the hills of Ashland, in a quiet country setting, 2 miles from downtown. The stone villa is an uniquely designed solar home, with abundant entertaining space both inside and out. There are two large, lovely view bedrooms, one upstairs, one downstairs. Each has a private...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Hopyard Views Farm - Minutes to Downtown Ashland!1 / 21
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Central Heating
    • Parking
    • Mountain Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 1, 2017
    We loved getting a glimpse of the hop harvest in progress just outside our door. Also, the couple that greeted us and lived in attached quarters was friendly and helped us...
    See all reviews
    About this property
    Just a quick five minutes from Downtown Ashland! Views of mountains, sheep, and chickens can be enjoyed from YOUR private deck, with (seasonal) hops, grapes and blackberries growing right outside your bedroom window This spacious modern suite is bright and comfortable, has a private entrance,...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Grill
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • Washer
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in the West Bedroom, a queen bed...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Hideaway Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, at just one and half blocks to the entry of the Theaters. The home features a full kitchen,...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Lawn Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, at just one and half blocks to the entry of the Theaters. The home features a full kitchen,...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This color blocked home shows off the beautiful spirit of life in Ashland. Just five blocks away from OSF, this home has a king bed in the upstairs sleeping loft and pull-out sofa 10' queen bed in the living room downstairs to sleep up to 4 people. It has a full kitchen with refrigerator, stove and...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    The High Street Cottage An Artists' Garden Cottage1 / 10
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Porch
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 4, 2016
    My boyfriend and I did "experience" gifts for each other at Christmas and this was mine to him. We loved it! Fantastic craftsman cottage with all the amenities you need...
    Reviewed July 10, 2014
    The High Street Cottage is our new favorite place to stay in Ashland. The cottage and grounds were beautifully maintained and thoughtfully stocked with coffee, tea, cooking...
    See all reviews
    About this property
    Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully equipped kitchen. A truly...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Mountain Views
    • Satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 2013
    Terra Cotta Cottage is a beautiful place to stay in Ashland. Every need has been anticipated with artistic thoughtfulness.Staying there was an experience in itself. From the koi...
    Reviewed April 11, 2013
    We thoroughly enjoyed our stay in Terra Cottage Inn. The space was perfect for our family of four with two young children. The beds were comfy for everyone. The whole...
    See all reviews
    About this property
    Nestled into one of Ashland's best neighborhoods, the Terra Cottage Inn is a clean and beautiful, hand-crafted artists' cottage. Full of art, hand thrown pottery, custom built furniture and all the amenities to make this a true luxury experience. Quality comfortable beds with high thread count...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    High above the hamlet of Ashland sits Bel Canto, your bungalow with views of the surrounding city and the east mountainside. The property features two private bedrooms, with a queen and full. The large living and dining area feature a sectional sofa and flat panel television. There is also a...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Country Cottage Apartment1 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Porch
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    This lovely cottage is absolutely perfect! It is clean, airy, and tastefully decorated. As you enter the cottage into the living room, you already feel how beautiful...
    Reviewed May 8, 2016
    This cozy cottage in a ranch setting was also a nice getaway from town. Organic eggs, local bread, butter and jam supplied by our host made us feel welcome and provided...
    See all reviews
    About this property
    Private cottage apartment with full kitchen and living area adjacent to family home. Covered porch and garden area to enjoy. Less than 15 minutes to Shakespeare Festival and downtown Ashland. Fresh eggs, local bread, jam, 1/2 and 1/2, milk and butter are stocked in fridge. There is also Nespresso,...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Central Heating
    • Satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Where the Southwest meets the Northwest... Views of Hyatt Lake, the Steel Trestle Bridge, the surrounding Alpine Forest... and just eighteen miles from downtown Ashland!...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Mountain Views
    • Porch
    • Outdoor Dining Area
    • Shared Yard
    • Parking
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    STAY <BR>Overlooking beautiful meadows, the light filled studio sleeps up to six with two queen beds in the loft rooms and a double sofa-bed downstairs. The Farrmhouse Studio also features a wood stove and a full kitchen stocked with dry goods. On-Farm Store has all our meats, sausages, eggs and...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • DVD Player
    • Patio
    • Wi-Fi
    • Waterfront
    • Hot Tub
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Just eighteen miles east of Ashland and POCKET VIEWS OF HYATT LAKE! Welcome to your Hyatt Lake Cabin, with a BBQ, and a large deck overlooking the forest, and pocket...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Just eighteen miles east of Ashland and the LARGEST CABIN AT HYATT LAKE! Just a three minute walk to Hyatt Lake, with a covered Hot tub, and a huge deck overlooking...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Inquiry
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn (scheduled for completion in Spring 2017) Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Inquiry
    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Balcony
    • Private Yard
    • Air Conditioning
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2017
    I would go back to Ashland just to stay here. Seriously. We were passing through on our way to California and needed somewhere tho spend the night. What a lucky accident! The...
    Reviewed November 12, 2016
    Just enjoyed 5 nights at the 2nd Street Cottages. Everything was perfect. We flew in from the east coast and got in close to midnight but Sugar was there to greet us. She...
    See all reviews
    About this property
    THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Parking
    • DVD Player
    • Central Heating
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Just eighteen miles east of Ashland and POCKET VIEWS OF HYATT LAKE! Welcome to your Hyatt Lake Cabin, with a BBQ, and a large deck overlooking the forest, and pocket views...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Come enjoy the peace & beauty of our pasture views on our ranch.1 / 22
    (6)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Patio
    • Hot Tub
    • Grill
    • Air Conditioning
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Inquiry
    Craftsman Style Home In Country Setting1 / 24
    (47)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Satellite TV
    • Internet Access
    • DVD Player
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Singing Birds Cabin, a real log cabin on 160 acres in the Cascade Mts.1 / 16
    (15)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Parking
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    ABBOTT'S COTTAGES - Delightful cottages - close to theatres1 / 9
    (4)Very good
    4 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Patio
    • Satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden1 / 24
    (68)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Historic Ashland Home with huge front porch and beautiful yard!1 / 9
    (5)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Make Inquiry
    Beautiful little place. Walk to town and theaters!1 / 11
    (18)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Patio
    • Parking
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Parking
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    Previous
    Ashland Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    64° 36°
    October
    48° 33°
    November
    43° 30°
    December
    43° 30°
    January
    Ashland Vacation Rentals

    Are you looking for the perfect vacation rental in Ashland, Ore.? Then come on in and take a look. Ashland, noted for its postcard picture perfect seasons, beautiful topography and friendly people, is the perfect vacation spot. Now that you’ve found it, you need someplace to stay. Rental cabins are a wonderful option and may be ideal for you and your family. Many are only a hop, skip and a jump from Ashland amenities, while affording you the privacy you desire. Make it a vacation to remember with a rental cottage, condo or cabin. With multiple price points and rental options, you’re sure to find something that fits your budget – and we can help.

    Ashland Activities

    If you’re looking for something to do while you’re in Ashland, head on over to the Oregon Shakespeare Festival. Each season brings something different for Shakespeare lovers ranging from tours to your favorite play. Other cultural events include the Oregon Cabaret Theater and the Ashland Independent Film Festival. Ashland is also home to more than 80 art galleries and multiple museums, such as the ScienceWorks Hands On Museum for children and the Ashland Art Center. From your home away from home vacation rental, plan your day around the activities that suit you best!

    Romancing Ashland

    Of course, with its beautiful location at the base of the Cascade Mountain Range, Ashland is perfect for lovers. Let us help you find a quaint rental cottage for two, while you focus on romance! Wine and dine with the best of them at several area restaurants including Chateaulin French restaurant. Here, you’ll find the perfect ambiance in the intimate and romantic dining room as well as an extensive wine list and gourmet French food. Or try the nationally acclaimed Winchester Restaurant at the Winchester Inn. Take your chocolate loving sweetie to the Oregon Chocolate Festival or go for a bike ride on the Mt. Ashland Mountain Bike Trail.

    Ashland is for Skiing and Golf

    With several mountain ranges in the Southern Oregon area, Ashland is perfect for the ski enthusiast! Hit the slopes at any one of the area resorts with trails ranging from beginner to professional, cross country to downhill. Find a rental cabin with access just outside your door and you’ll be in ski heaven. Located at 7,500 feet, Mt. Ashland offers skiing during the season from November to April on a variety of trails for any skill level as well as snowboarding. Golf resorts include Oak Knoll in Ashland and Centennial Golf Club in nearby Medford.

    List your property
    Owner log in