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Madison Vacation Rentals

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    $209 Average
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    Don't let other travelers get your favorite Madison area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Madison
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    Madison
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Madison
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Madison
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Madison
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Madison, Virginia 22727
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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    Madison
    6 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Balcony
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Madison, Virginia 22727
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 18
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    The following rentals are within 15 miles of Madison.
    Spruce Creek Retreat: White Oak Canyon/Old Rag Mt1 / 22
    (1)Excellent
    Syria
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Mountain Views
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 4, 2016
    I stumbled upon this gem while looking for a place to take my husband to for his birthday. I initially wanted something in a hotel close by to great hiking trails, but soon...
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    About this property
    Spruce Creek Retreat is a 3000 sq ft house on the bank of the Robinson River. It's located adjacent to the Shenandoah National Park and less than 1 mile from the White Oak Canyon and Cedar Run trailheads. These trails offer some of the best waterfall hiking in the Shenandoah National Park. The...
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    Syria, Virginia 22743
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Walk to White Oak Canyon Hiking Trail & Falls1 / 15
    (5)Very good
    Syria
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Porch
    • Air Conditioning
    • Mountain Views
    • Parking
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2013
    This cottage was the perfect Labor Day weekend getaway! Perfect location to White Oak Canyon and Old Rag hiking trails. The cottage was very clean upon our arrival. The owner...
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    About this property
    White Oak Canyon Cottage is a cozy cottage nestled in a beautiful valley of the Blue Ridge Mountains near the Robinson River and Cedar Run. It is located adjacent to the Shenandoah National Park and is literally steps from the White Oak Canyon Hiking Trail and Cedar Run Hiking Trail lower...
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    Location Information
    Syria, Virginia 22743
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Boston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you ever wanted to visit an Olde English Home, this home as a huge stone fireplace, 10 foot beamed ceilings, wood floors, leather sofa, tapestry. It's a unique and interesting for comfortable stay in the country. While a couple might find the first floor perfectly adequate for a romantic get...
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    Location Information
    Boston, Virginia 22713
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Barboursville Cottage at Sugar Plum Farm1 / 16
    (1)Very good
    Barboursville
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Yard
    • Air Conditioning
    • Housekeeping Included
    • Hot Tub
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 25, 2016
    The cottage was beautiful and well kept, the hot tub was fabulous, and the location next to Barboursville Winery was great (we walked there twice). We were originally looking...
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    About this property
    Nestled in the foothills of the Blue Ridge Mountains just 20 minutes north of Charlottesville and 30 minutes east of Shenandoah National Park, the Barboursville Cottage at Sugar Plum Farm offers a peaceful oasis in central Virginia's wine country with easy access to outdoor recreation, winery and...
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    Location Information
    Barboursville, Virginia 22923
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Ruckersville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer the lower level walkout of our home with full size windows in every room, on 5 acres of complete privacy, with views of the Blue Ridge Mountains from the front porch. It's an excellent place to enjoy morning coffee! The peacefulness of this property can only be truly appreciated upon a...
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    Location Information
    Ruckersville, Virginia 22923
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The Cabins at Rose River Farm1 / 21
    (83)Excellent
    Syria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    • Porch
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    Just wanted to send you a note letting you know how much we enjoyed our stay at the Hill Top cabin. That area is a beautiful part of our state and your accommodations were 1st...
    Reviewed 5 days ago
    Thank you for opening your farm to us for what has become our favorite vacation spot of the past decade. My husband and I thoroughly enjoyed the beauty of the valley and the...
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    About this property
    Rose River Farm features three exceptional rental cabins that are modern day interpretations of classic Mongolian Yurts. Constructed of cedar, glass and steel the cabins are over 1,100 square feet each and feature two bed rooms with two full baths. Each bedroom has two double beds. The living...
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    Location Information
    Syria, Virginia 22743
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Orange
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront property is located on the calm northern end of Lake Anna. It is a custom timber-frame home designed by Vermont architect Davis Weigand. The upscale kitchen will be a delight for the cook in your family or grill out on the deck overlooking the Lake. The two master bedrooms each have...
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    Location Information
    Orange, Virginia 22960
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Secluded Cottage with Spectacular Mountain Views1 / 20
    (28)Excellent
    Ruckersville
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Washer
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 28, 2015
    We really enjoyed our visit at the cottage. We chose this location so that our dogs could come along and have a lot of room. The view is breathtaking and we loved the...
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    About this property
    Located on 80 beautiful acres with panoramic views of the Blue Ridge Mountains, this cozy three-bedroom cottage is the perfect location for exploring Charlottesville and the surrounding area. Tour local historical sites, visit local vineyards, shop for unique antiques, indulge in exquisite cuisine...
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    Location Information
    Ruckersville, Virginia 22968
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Stanardsville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EXPERIENCE A STUNNING BLUE RIDGE MOUNTAIN VACATION ON A PRIVATE FARM! Delight in the bold views of the Blue Ridge Mountains while lounging on your private covered porch at the Carrie's Cottage on Fairhill Farm, a working farm of 142 acres and adjacent to our 130 acre High Fields Farm. Stroll on...
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    Location Information
    Stanardsville, Virginia 22973
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Echo Valley Farms by the Shenandoah National Park1 / 30
    (1)Excellent
    Stanardsville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Housekeeping Included
    • Parking
    • Grill
    • Hot Tub
    • Satellite TV
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2016
    This was the perfect cabin for our trip! We each had our own bed and two bathrooms with showers was plenty of space. We loved the large upstairs sitting room and the view of...
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    About this property
    Resting on 28 acres at the foot of the Blue Ridge Mountains, Echo Valley Farm is a place that will make your entire body relax from the moment you step foot on the property. The bones of this property date back to the early 20th century, but the house has been completely renovated with all the...
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    Location Information
    Stanardsville, Virginia 22973
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    High Fields Farm with stunning mountain views, private pool, hiking, pond,& more1 / 48
    (7)Excellent
    Stanardsville
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Satellite TV
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2013
    We had a lovely stay at Carrie's Cottage to celebrate my daughter's seventh birthday. The cottage and grounds were exactly as described, and Alton was the consummate host. We...
    Reviewed March 2, 2012
    My husband and I rented this house with our 4-month old, plus two other couples and their 4-month olds for a long off-season weekend. It was a nutty idea as none of us slept...
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    About this property
    Stunning Blue Ridge Mountain views! Whether a romantic weekend getaway, a gathering of family and friends, an anniversary, or a week-long family vacation, we invite you to experience the luxury of our unique vacation rentals on our two large farms, comprising nearly 300 acres, at our Fairhill Farm...
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    Location Information
    Stanardsville, Virginia 22973
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Boston
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Private Yard
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfy converted horsebarn offers you all the amenities without the horses. You have a full kitchen, living room, dining area, private deck and lawn area for BBQ and a fanatic view of the 3 acre pond which provides endless day and night enjoyment. Another view is the pasture with the sheep...
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    Location Information
    Boston, Virginia 22713
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Somerset
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Secure Parking
    • Satellite TV
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the perfect place for a wedding weekend, a family reunion or just a wonderful country getaway, look no further. Spotswood Lodge is an 11-acre Farm with a pond and a beautifully decorated House & Cottage located in gorgeous Central Virginia. Perfectly located between the Towns...
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    Location Information
    Somerset, Virginia 22942
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Orange
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just outside the town of Orange, Virginia, The founders of Grelen Nursery & The Market at Grelen have renovated this lovely 1891 home to add to their event & lodging options for their Market at Grelen guests and area visitors. In good shape structurally, this gem just needed a little...
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    Location Information
    Orange, Virginia 22960
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Stanardsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Yard
    • Satellite TV
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EXPERIENCE A STUNNING BLUE RIDGE MOUNTAIN VACATION ON A PRIVATE FARM! Delight in the bold views of the Blue Ridge Mountains while lounging on your private deck at the Carriage House on Fairhill Farm, a working farm of 142 acres. Stroll on farm or hike our private trails. Fish in private pond or in...
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    Location Information
    Stanardsville, Virginia 22973
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chestnut Hills Cottage1 / 12
    (2)Excellent
    Stanardsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Balcony
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 7, 2016
    We stayed at Chestnut Hills Cottage for the weekend to attend a wedding in Stanardsville. The cottage is beautiful, clean, and very well-maintained. The host made check-in super...
    Reviewed October 20, 2016
    I rented here to attend a wedding because it is almost the same cost as hotel. I was very impressed with the property and would love to stay again. It would be a perfect...
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    About this property
    Welcome to Chestnut Hills Cottage! A charming, well appointed escape from city life. Our cottage offers a private, tranquil and romantic environment to help you rejuvenate and relax. Whether Star Gazing from the Hot Tub, or heading out for adventures at the numerous nearby wineries and National...
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    Location Information
    Stanardsville, Virginia 22973
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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