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 with Pools in Berkshires

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
    $522 Average
    |||
    |||
    $0$2,000+
    Suitability
    Suitability
    More filters
    Travellers to Berkshires are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in BerkshiresView all 125 rentals
    Sort by:
    Default
    Wyndham Bentley Brook at Jiminy Peak1 / 21
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Berkshires: Romantic Cottage with spectacular view1 / 18
    (23)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Balcony
    • Shared Indoor Pool
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our home on Jiminy Peak! This beautiful, luxury unit was just renovated for the 2016 ski season. It is fully equipped with everything a family will need for the perfect Mountainside vacation. Two Bedrooms accommodates 6+ guests with all the comforts of home. 10 foot ceilings and crown...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please email or call to confirm availability. Ski-In/Ski-Out Resort! Wyndham Bentley Brook is located right at the base of Jiminy Peak ski mountain, with ski lifts only 200 feet from the resort's front door. In winter, you can ski right out the door to the lifts. In spring, summer and fall,...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have this in both 1 and 2Br, so please confirm which you want. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for a...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Jiminy Peak Luxury Ski In/Ski Out Home1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Indoor Pool
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2018
    We had 10 people and everyone had a real bed!! The decor is wonderful, and ski in ski out on a green trail allowed us to not get into the car all weekend.
    See all reviews
    About this property
    Steps from the main lifts this 3 Bedroom unit can accommodate up to 8 guests; with all the comforts of home. Master bedroom, with Queen-size bed, wall mounted TV, large closet and a view of the Cricket lift and learning slope. The master bath has duel sinks, jet tub, body sprays and washer and...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is an exact replica of the first Colonial ever built in Massachusetts back in the 1600's. It is called the 'Parson Capens Home' and is located in Topsfield Mass. It has the design of the old but all the modern features. The home is nestled in the mountains of Berkshire County which have...
    View all property information
    Location Information
    Dalton, Berkshires 01226
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!...
    View all property information
    Location Information
    Lee, Berkshires 01238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2017
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
    See all reviews
    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath...
    View all property information
    Location Information
    Alford, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Berkshires rentals sent straight to your email!
    Get the List
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 October 2015
    Beautifully decorated house nestled in the Berkshires. A true getaway. Plenty of room for a family with the latest TV/computer set up. Big kitchen with the best appliances...
    See all reviews
    About this property
    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the...
    View all property information
    Location Information
    Sheffield, Berkshires 01257
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation Village in the Berkshires accommodations feature spacious floor plans for maximum comfort. Kitchen, living and dining room in each suite are integrated for entertaining and enjoyment. Designated suites meet Americans with Disabilities Act (ADA) requirements. Unit Features Individual...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
    Make Enquiry
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Indoor Pool
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have qty 2 units available .$1400 each Dec 22 through Dec, 29th-2017 $2650 for both units . Wyndham Bentley Brook / Jimminy Peak Ski Resort ,features indoor and outdoor swimming pools and hot tubs, two fitness centers, sauna, game room, three tennis courts and a picnic/BBQ area, downhill skiing,...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book a one-of-a-kind stay in this 5-bedroom, 4.5-bathroom vacation rental home in South Egremont. Built from the bones of a 15th-century British barn, this 4,000-square-foot home for 10 is one of the oldest structures in Massachusetts! Whether you were drawn to the Berkshires by the natural beauty...
    View all property information
    Location Information
    North Egremont, Berkshires 01258
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Shared Indoor Pool
    • Terrace
    • Air Conditioning
    • Internet Access
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thanksgiving week Berkshire Luxury condo/4 1Bedroom, 1Bath, Living Room with fireplace & Kitchen Available November 20-27 Thanksgiving week Between Mt. Greylock, Pittsfield, Great Barrington, Stockbridge, Krupalu, Tanglewood, Jacob's Pillow, The Mount, NOrman Rockwell Museum, Daniel Chester French...
    View all property information
    Location Information
    Williamstown, Berkshires 01267
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    8 Bedrooms, 10 Bathrooms, Sleeps 17 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Stockbridge MA Bed & Breakfast is the closest Inn and within walking distance to the Norman Rockwell and Chesterwood Museums. Nestled on 4 private acres of Berkshires landscape, we offer top quality B&B lodging accommodations that is centrally located to all major area attractions. A Federal...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Private Room - 8 Bedrooms, 10 Bathrooms, Sleeps 17
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Washer
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! Nestled along the scenic border of New York and Massachusetts in the middle of Jiminy Peak Mountain Resort, this pristine Hancock vacation rental condo comfortably...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    List your property
    Owner log in