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.

Greenfield 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
    Location
    Any Distance
    from
    Price
    per night
    $219 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Greenfield area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Greenfield
    Sort by:
    Default
    Greenfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 20 miles of Greenfield.
    Unique People & Pet-Welcoming Country Haven1 / 37
    (174)Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Stone 'n Sky Lodge on an Ancient Stone Landscape1 / 32
    (5)Excellent
    New Salem
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Flight's End-A Country Home with Babbling Brook1 / 22
    (9)Very good
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 3, 2017
    We needed a much needed break from the hustle and bustle of the city and we found the perfect place. Flight’s End was secluded, had a lot of empty space for our four legged...
    Reviewed August 26, 2017
    We booked Flight's End for our recent mini vacation and were extremely pleased. The house is definitely a place where people lived and grew old, and had a comfortable...
    See all reviews
    About this property
    3 Bedroom house, know as Flight's End, is for rent by day, weekend, week or month. Great for romantic get away or a family outdoor vacation. Not a party house. Fifteen minutes to Charlemont, Ashfield and Shelburne Falls. House is located on a brook and across the road from a private pond (not...
    View all property information
    Location Information
    Hawley, Massachusetts 01339
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The White Room has a single queen sized bed and a beautiful cherry desk built by your host, John. This room has its own bathroom (ensuite) with a shower, toilet, sink, and toiletries. Sitting at the desk, you will see the east pasture where the llamas like to sleep in the summer. The rear window...
    View all property information
    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Charming Affordable  Home for groups up to 141 / 11
    (9)Excellent
    Shelburne Falls
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 3, 2014
    I stayed in this house with a group of about 14 friends from college (we're a few years out) the weekend after Christmas, and we had a great time staying at Susan's place in...
    Reviewed July 3, 2012
    The home was so perfect. Just a short walk to the center of Shelburne Falls, 5 minute drive to rafting outfitters, swimming holes.Huge house with a great kitchen, but you'll...
    See all reviews
    About this property
    Our 7 bedroom, 3 bath, redone Federal House is the perfect place for family celebrations, school reunions, wellness, writing, quilting or other special interest gatherings. Your whole group can share our dining area and even enjoy the services of a gourmet chef should you desire. We have 8 quiet...
    View all property information
    Location Information
    Shelburne Falls, Massachusetts 01370
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Inquiry
    Berkshire house w/ fireplace, A/C, WiFi & laundry1 / 27
    (16)Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Housekeeping Included
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2014
    The home and grounds were lovely but need some updating,and a good cleaning. Location was secluded with plenty of forest and hiking trails, and a scenic lake for fishing. The...
    Reviewed May 29, 2014
    We all thoroughly enjoyed our long weekend at this lovely house. It was spacious, well situated, and well equipped. We were sorry our stay was so short, and the time in the...
    See all reviews
    About this property
    Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone. We like to define our country...
    View all property information
    Location Information
    Plainfield, Hampshire County 01070
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    Lakefront Summer Vacation Cottages1 / 16
    (4)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Waterfront
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 2018
    Wonderful Labor Day weekend trip with our grandchildren, ages 5 and 8, and out 2 year old Great Pyrenees. Clean and comfortable cottage, appropriately stocked kitchen, and the...
    Reviewed April 20, 2018
    This review is a little late but we lived here last August through October while I was working in the area. We loved it. The Lake and the views were from late summer through...
    See all reviews
    About this property
    We have shared the beauty of our lakefront property for many summers. We live on the property year round and rent three cottages from late June through September.We love our guests and honor their privacy. We are a family and pet (dog) friendly vacation spot,unique and enjoyable! The property is...
    View all property information
    Location Information
    Goshen, Hampshire County 01032
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Stunning Lakefront home on crystal clear, sandy bottomed, 110 acre Forest Lake at the junction of NH,VT,& MA will be your long awaited retreat in the whispering pines, shimmering lakes, and beautiful foliage of New Hampshire. Bring the kids & dogs or just enjoy by yourselves. The Great room with...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    PARADISE on EARTH! - Historic 4BR Farmhouse1 / 7
    (1)Excellent
    West Halifax, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Porch
    • Wi-Fi
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 16, 2015
    We rented this house to be close to Mount Snow so our boys could spend their vacation snowboarding. The house was as beautiful as described. The rooms were charming and...
    See all reviews
    About this property
    • 19th Century Farmhouse with beautiful mature gardens • 24 Park like acres - woods and streams • Perfect location to attend Marlboro Music Festival • Close to Brattleboro (10 miles) located in the Village of West Halifax • House has 4 bedrooms - 2 master bedrooms with Queen Beds • 2...
    View all property information
    Location Information
    West Halifax, Vermont 05358
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Save time - get the best Greenfield rentals sent straight to your email!
    Get the List
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Actually, the Pink room is painted a lovely 'Santa Fe red' and is a mirror image to the White Room. The Pink room has a single queen sized bed, and its own bath in the room (ensuite) with a shower, toilet, freestanding sink, and toiletries. Sitting at the spinette (an antique desk that once housed...
    View all property information
    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Conway
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming one-bedroom apartment situated on 8 beautiful and peaceful acres in the rolling hills of Conway Massachusetts. The apartment has a large kitchen, a sitting room, study 'nook', private bath with laundry facilities and a separate entrance. Guests are greeted every morning by two friendly...
    View all property information
    Location Information
    Conway, Massachusetts 01341
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    Adorable Studio apartment in Brattleboro1 / 5
    (2)Average
    Brattleboro, VT
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Central Heating
    • Outdoor Dining Area
    • Grill
    • Shared Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2016
    You can't beat the location just off I-91, 5 minutes (15 if you walk) from downtown Brattleboro. The hosts were very nice and helpful, and we loved their cats and dog, when...
    See all reviews
    About this property
    Welcome to the Culbertson House! This adorable studio apartment was completely refinished a few years ago. It features a gorgeous stone fireplace, tasteful furnishings and decoration, a comfortable king-size bed, fully equipped kitchen, full bath with shower, and exquisite hardwood walls and floor....
    View all property information
    Location Information
    Brattleboro, Vermont 05301
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Inquiry
    Amherst
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Housekeeping Included
    • Balcony
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Possibly the best apartment location in Amherst for those who love our quaint town. Right downtown, walking distance to restaurants, pubs, boutiques and cafes. A few feet from the free PVTA bus to UMass and all the 5 Colleges. You can walk to UMass and Amherst College. Two bedrooms with an open...
    View all property information
    Location Information
    Amherst, Hampshire County 01002
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and...
    View all property information
    Location Information
    Hatfield, Hampshire County 01038
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    Vermont Log Cabin available for weekend and weekly1 / 5
    (7)Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 2017
    Beautiful mountain retreat! Has all of the comforts of home minus wifi and cell service. A perfect way to unwind and disconnect. Pictures do not do this quaint log cabin...
    Reviewed May 30, 2014
    The word "cabin" doesn't do this property justice. It is actually a comfortable two bedroom log home which is immaculate and well secluded. There is no internet service...
    See all reviews
    About this property
    If you want to get away from the hustle and bustle of our technologically driven lives and slow down, breath and relax, our cabin is the perfect place for you. No phones, television or internet, just a nice comfortable and affordable country log cabin nestled in the foothills of the Green...
    View all property information
    Location Information
    Guilford, Vermont 05301
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lavender Room, or Inside room as we often call it, is nestled inside the house, and is located off the kitchen. It is the largest of the three rooms and was recently painted a lovely 'amethyst' or rich lavender color. Its bathroom, while not in the room, is located directly across the private...
    View all property information
    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Winchester, NH
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private one bedroom on the site of The Outlaw Brewing Company. Enjoy the country life while enjoying locally made craft beer. Lots to do for adventerous couples. Visit local breweries, distilleries and wineries. Hike Pisgah State Park, Mount Monadnock, Madame Sherri's Forest or Pulpit Falls. Make...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Beautiful Lake Side Getaway, Quiet, and Peaceful1 / 21
    (4)Excellent
    Winchester, NH
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 30, 2014
    Great off the beaten track place to stay yet only 20 minutes from Keene. Bill and Sandie very gracious hosts both before and during your stay. Accommodations very modern. We...
    Reviewed July 12, 2014
    My fiancé and another couple stayed here for a few days in May. It was absolutely beautiful and exactly what we were looking for! My fiancé and I are avid "outdoors...
    See all reviews
    About this property
    New Hampshire Meals & Rentals Operator's License #063697 2 Bedrooms, 1 bath, sleeps 6. Private beach, dock, raft, rowboat, canoe, 5 Kayaks, or launch your boat. Cable TV, high speed internet, WIFI, 42' flat screen internet TV. Sleeps 6 - two bedrooms - One with Queen Bed, one with two single beds...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Whitingham, VT
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Discounts and seasonal specials may be available - call Evolve at (877) ******** for more info! ** James Gandolfini stayed here! 'Mount Snow Farm' is a 120-acre former dairy farm and secluded haven nestled in the Green Mountains near Whitingham, Vermont. The top of this property sits 2,300...
    View all property information
    Location Information
    Whitingham, Vermont 05361
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    new condo with open floor plan and first floor master with view across the Connecticut River to Mount Holyoke. Quartz countertops and high end appliances make it a dream kitchen. Master bedroom has steam shower and soaking tub. Second floor has one single bedroom (with room for inflatable bed or...
    View all property information
    Location Information
    Hatfield, Hampshire County 01038
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the New England woodlands and reconnect with the outdoors when you stay at this 2-bedroom, 1-bathroom Goshen vacation rental cabin that sleeps 8. This quiet, 725-square-foot cabin offers peace and comfort, with an open-concept living space, a large deck with a patio set and grill, a...
    View all property information
    Location Information
    Goshen, Hampshire County 01032
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Inquiry
    Shelburne Falls
    Studio, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Central Heating
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your bags for a peaceful nature retreat at this charming vacation rental studio cabin! Ideally situated on 65 expansive acres, this Shelburne escape offers accommodations for 6 and upgraded amenities such as a floor-to-ceiling fieldstone fireplace and stainless steel appliances. Whether you're...
    View all property information
    Location Information
    Shelburne Falls, Massachusetts 01370
    Condo/Apartment - 1 Bathroom, Sleeps 6
    Make Inquiry
    Hatfield
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape the boring and embrace the unique when you stay at this vacation rental home in West Hatfield. The house was custom built in 2014 and boasts 4 bedrooms, 2 bathrooms, and room for 8! The property includes 7 acres of a beautiful wooded area and is near the River Valley Co-op where you can...
    View all property information
    Location Information
    Hatfield, Hampshire County 01088
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tibet House is a beautifully decorated and comfortably furnished private apartment on a quiet tree lined street just 3 blocks from Smith College and downtown Northampton. The Parlor Room, The Iron Horse, The Academy of Music and The Calvin Theater are all just a short walk away. There is plenty of...
    View all property information
    Location Information
    Northampton, Hampshire County 01060
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    Greenfield Flight and Weather Info
    Airports nearby (1)
    Plan your day of travel
    BDL
    Bradley Intl Airport
    45.2 miles from Greenfield
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    26°
    January
    30° 10°
    February
    36° 18°
    March

    Additional Greenfield Info

    Go to map view
    • Local time: 07:39 AM (EST)
    List your property
    Owner log in