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.

Spencertown House 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
    $393 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Spencertown area vacation rental. You're so close to securing your perfect getaway. Book today.
    23 Matching Rentals in the Spencertown AreaView all 43 rentals
    Sort by:
    Default
    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 10 miles of Spencertown.
    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Berkshire Country Estate - The Library Suite1 / 21
    (1)Excellent
    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Great Vacation House in the Berkshires on Richmond Pond1 / 10
    (4)Excellent
    Richmond, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    Being Tanglewood lovers, this was the perfect vacation spot to enjoy the area's concerts, plays, art galleries and restaurants as well as the lovely Richmond Pond and the...
    Reviewed August 27, 2017
    This comfortable, breezy house was perfect! We loved being able to walk to the lake and canoe, play frisbee on the lawn, walk in the woods, eat on the deck, and gaze at the...
    See all reviews
    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers...
    View all property information
    Location Information
    Richmond, Berkshires 01254
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Beautiful Vacation Home1 / 32
    (5)Excellent
    Stockbridge, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 18, 2017
    Our 4 families stayed here for a long ski weekend and had the best time! The home is beautiful-- and had plenty of space for all of us! The home was fully stocked with...
    Reviewed November 9, 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
    See all reviews
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Inquiry
    Enjoy Autumn in New England. Fall festivals, comfort foods, leaf peeping hikes.1 / 18
    (7)Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed August 27, 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    See all reviews
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination, a haven, a state...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Stockbridge, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic River just across the street,...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Inquiry
    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    West Stockbridge, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 26, 2018
    We had a large group staying at the house with kids and had a great experience. Elaine is very thoughtful, helpful and attentive. She obviously cares about the house and makes...
    Reviewed November 14, 2017
    Elaine was a pleasure to communicate with and made us feel right at home. The home is just how it looks in the pictures. If you're searching for a comfortable, clean, and cozy...
    See all reviews
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Inquiry
    Stockbridge, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master...
    View all property information
    Location Information
    Stockbridge, Berkshires 01238
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Save time - get the best Spencertown rentals sent straight to your email!
    Get the List
    Newly Renovated Colonial on the River! Sleeps 5-61 / 20
    (1)Excellent
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updated and outfitted for modern day convenience but retains its charm and unique...
    View all property information
    Location Information
    Stockbridge, Berkshires 01236
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Shared Yard
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes...
    View all property information
    Location Information
    Austerlitz, New York 12017
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be enjoying a newly renovated space with Calcutta marble floors throughout. The house features 2 bedrooms at opposite sides of the house to provide more privacy. A luxurious bathroom with a Roman soaking tub and marble mosaics. A totally loaded kitchen and great outdoor space which...
    View all property information
    Location Information
    Ghent, New York 12075
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the center of Columbia County, NY this retreat is a great spring board to all it has to offer: minutes to Hudson, Chatham, High Falls, hiking trails, farms, streams. You’ll love the varied bright cozy rooms to lounge in, including a screened front porch. Most relaxing is to hang out on...
    View all property information
    Location Information
    Philmont, New York 12534
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Stockbridge, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Yard
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **1 week minimum July & August** Just 1 1/2 to the Red Lion Inn in Downtown Stockbridge, Tanglewood, Norman Rockwell Museum, Private country setting just across from the Housaitonic River. Our newly built home pairs a traditional shingle style exterior with an open & slightly modern interior. The...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Austerlitz
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Hot Tub
    • Central Heating
    • Balcony
    • Grill
    • Patio
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beautiful renovated Georgian Colonial home sits amongst 40 acres of natural beauty. The house overlooks a serene pond and all its beauty with views of natural forrest beyond. The house itself has a oversized chef's eat in kitchen. The Kitchen has all the amenities to host wonderful meals and...
    View all property information
    Location Information
    Austerlitz, New York 12017
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Inquiry
    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 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
    This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms...
    View all property information
    Location Information
    Hillsdale, New York 12529
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Inquiry
    Old Chatham
    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires, only 2 1/2 hours from New York City and Boston. Surrounded by the beauty of the Berkshires, the estate is very private, with a 1/8 mile driveway leading to the 10 acre front lawn. A large elegant, yet...
    View all property information
    Location Information
    Old Chatham, New York 12136
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 16
    Make Inquiry
    Richmond, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
    View all property information
    Location Information
    Richmond, Berkshires 01254
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Richmond, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation home has something for everyone! If you're a culture vulture, outdoor enthusiast, or just want the peace and quiet of the country, this 4 bedroom home in the Berkshires is for you! It is 15 minutes from Lenox and Tanglewood, 10 minutes from shopping, restaurants and several theatres,...
    View all property information
    Location Information
    Richmond, Berkshires 01254
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • Housekeeping Included
    • Balcony
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated 1800s farm house on 100 acres with heated in ground gunnite pool, hiking trails located on a beautiful creek. We also have a guest house with two more bedrooms and a full kitchen by the pool that is perfect for bringing your in-laws or babysitter. The house has a chef's kitchen...
    View all property information
    Location Information
    Chatham, New York 12037
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Inquiry
    NEW! 'Butterfly Hill' 2BR West Stockbridge House1 / 24
    (1)Excellent
    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2018
    We thoroughly enjoyed our week at Butterfly Hill. It was near Tanglewood, our main reason for the visit, and all the nearby towns where we found good restaurants and shops. We...
    See all reviews
    About this property
    Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provide the perfect...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Spencertown Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    55° 35°
    October
    42° 27°
    November
    32° 18°
    December

    Top-rated Spencertown Things to Do

    Browse all things to do

    Additional Spencertown Info

    Go to map view
    • Local time: 01:45 AM (EDT)
    List your property
    Owner log in