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.

Holiday Rentals and Apartments in Stephentown, NY and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    $0
    $310 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Stephentown area holiday rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    Stephentown
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    From
    $834
    / Night
    Payment Protection
    View Details
    View Details
    1 / 16
    4 of 5 stars (2) Very good
    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    other travellers have booked this property
    From
    $208
    / Night
    Payment Protection
    View Details
    View Details
    Stephentown
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $215
    / Night
    Payment Protection
    View Details
    View Details
    Stephentown
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $347
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Balcony
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Washer
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This cozy cottage is perfect for a small group of friends or a family getaway in the beautiful Berkshires. We're on 120 acres of private woods but only 7 miles from Jiminy Peak. The main space features a cathedral ceiling in the open living/dining area, with a glass-front woodstove for chilly... View all property information
    Location Information
    Stephentown, New York 12168
    1 / 24
    5 of 5 stars (4) Excellent
    Stephentown
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $556
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Mountain Views
    • Parking
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Countryside setting with a fantastic view of the Berkshires and centrally located. 10 minutes to Jiminy Peak ski area, 30 minutes to Tanglewood, 25 minutes to Stockbridge, 20 minutes to Mt. Greylock, 25 minutes to Williamstown theater. the lodge has a 500 square foot grand room for parties,... View all property information
    Location Information
    Stephentown, New York 12168
    5 of 5 stars Reviewed 21 November 2015
    I attended a group weekend workshop at the Berkshire Blueberry Lodge in Stephentown; foothills of the Berkshires. I cannot tell you how beautiful the lodge is; the breathtaking...
    5 of 5 stars Reviewed 14 September 2015
    We stayed in Blueberry Lodge with my fiance and family during Labor Day weekend. We loved the house which was comfortable and spacious enough for 8 of us. Breathtaking view from...
    See all reviews

    The following rentals are within 10 kilometres of Stephentown, New York.

    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $486
    / Night
    View Details
    View Details
    Amenities & Details
    • Skiing: Property Is...
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 23 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    4 of 5 stars Reviewed 27 January 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
    See all reviews
    Hancock, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $181
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Hot Tub
    • DVD Player
    • Internet Access
    • Satellite TV
    • Mountain Views
    • Washer
    • Sauna
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Sledding on back terrace. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and... View all property information
    Location Information
    Hancock, Berkshires 01237
    Hancock, MA
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $243
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Washer
    • Sauna
    • Patio
    • Balcony
    • Mountain Views
    • Hot Tub
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pool. Go hiking, biking, fishing or horseback riding around the property or enjoy the off site... View all property information
    Location Information
    Hancock, Berkshires 01267
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $1,668
    / Week
    Payment Protection
    View Details
    View Details
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ***Price and availability subject to change without notice*** Bentley Brook, located in the Jiminy Peak ski area, offers a variety of on-site amenities -- from downhill skiing to swimming and biking. The Berkshire area also provides a vast array of cultural and historic attractions. Visit... View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 4
    4 of 5 stars (1) Very good
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    From
    $318
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
    Location Information
    Hancock, Berkshires 01237
    4 of 5 stars Reviewed 11 August 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    From
    $124
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Private Indoor Pool
    • Sauna
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Discover an unparalleled vacation destination at Wyndham Bentley Brook. This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal activities, return to your... View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    From
    $313
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Mountain Views
    • Grill
    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
    Location Information
    Hancock, Berkshires 001237
    5 of 5 stars Reviewed 8 October 2010
    We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended...
    4 of 5 stars Reviewed 7 October 2010
    My husband and I stayed here with our 2 teen age girls last summer. We looked for a house that was close to Jiminy Peake for a family gathering. The house was well equipped and...
    See all reviews
    1 / 19
    5 of 5 stars (1) Excellent
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    From
    $346
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 10 September 2015
    The units are clean and spacious and well stocked. Movie theater, swimming pools, outdoor picnic area with grills. and the mountain adjacent has plenty of outdoor activities...
    See all reviews
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock, MA
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    From
    $202
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
    5 of 5 stars Reviewed 17 October 2014
    This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
    See all reviews
    1 / 25
    5 of 5 stars (8) Excellent
    Hancock, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $417
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Washer
    • DVD Player
    • Central Heating
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 8 July 2015
    My eight year old daughter and I had a wonderful time staying in Hancock. We were joined at different times by young cousins and grandparents - the kids loved the inside (the bunk...
    5 of 5 stars Reviewed 12 October 2014
    Stayed here for a couple nights over labor day to get out of the city. The place is perfect for a group of 4 and even better for our 2 dogs. Great little creek for them to go...
    See all reviews
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    From
    $313
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Hot Tub
    • Sauna
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 16
    4.5 of 5 stars (2) Very good
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    From
    $263
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 6 September 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    4 of 5 stars Reviewed 26 October 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
    See all reviews
    Hancock, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveller has booked this property
    From
    $347
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
    Location Information
    Hancock, Berkshires 01237
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $282
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Washer
    • Satellite TV
    • Grill
    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook has... View all property information
    Location Information
    Hancock, Berkshires 01237