Holiday rentals with a hot tub in Pittsfield

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Top-rated rentals with a hot tub in Pittsfield

Guests agree: these rentals with a hot tub are highly rated for location, cleanliness and more.

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An old-fashioned cedar hot tub is positioned on a wooden deck, surrounded by trees displaying autumn foliage. The peaceful outdoor setting offers a serene atmosphere for relaxation.
Cabin in Stephentown
4.85 out of 5 average rating, 308 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Top guest favourite
A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.
Home in Colebrook
4.99 out of 5 average rating, 233 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

Top guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 328 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favourite
A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.
Place to stay in North Adams
4.93 out of 5 average rating, 169 reviews

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Guest favourite
Flat in Waterford
4.91 out of 5 average rating, 318 reviews

HOT TUB & New Stylish Saratoga County Efficiency

About the space Brand New Everything. This newly created space offers city style interior decor with outside space to enjoy. This includes the New Trex deck with HOT TUB and outdoor relaxation. Situated on large lot- this space offers convenient access to local highways (5 min from I-87, 10 min from 787). Off street parking for 2 vehicles. RV, boat, trailer space available on site. Within 2 min -be at convenience store, pizza shop, ice cream, mini golf, town park and more..

Guest favourite
A renovated Airstream is nestled among lush greenery, featuring large windows and a deck with dining setup. Soft lighting from overhead string lights adds a warm ambiance, while surrounding trees enhance the peaceful, natural setting.
Cabin in West Sand Lake
4.96 out of 5 average rating, 364 reviews

The Airstream at June Farms

Our 1984 Airstream has been renovated with interior design and comfort in mind. This little oasis in the woods will give you peace and quiet, and a luxury salt water hot tub to help keep soak the stress away. Please check our availability for our other luxury cabins if The Airstream is booked! If the Airstream is booked during the week on dates that you would like, but The Lodge is available, let us know and we can give you The Lodge for the same rate!

Top guest favourite
The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.
Home in Monterey
4.96 out of 5 average rating, 281 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Guest favourite
A yellow sign is displayed among green foliage, featuring a goat and two ducks illustrated on it. The bold text indicates 'SLOW FREE RANGE DUCKS & GOATS at PLAY,' emphasizing the friendly atmosphere surrounding the property.
Farm stay in Ancram
4.96 out of 5 average rating, 362 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

Guest favourite
The kitchen features green cabinetry with a white countertop. Shelves above hold various jars and glasses. A window allows natural light to brighten the space, with a view of nature visible outside. Additional storage includes a fridge and a stainless steel trash bin.
Cabin in Athens
4.95 out of 5 average rating, 114 reviews

Charming Lakefront Cabin with Hot Tub

Thoughtfully updated lakefront cabin, north of the Catskill mountains, in the Hudson Valley. Located inside the private, family-friendly Sleepy Hollow Lake community with guest access to pools, beach, tennis courts, & basketball (May-Sep). A peaceful retreat - come watch the hummingbirds from the porch or have your morning coffee looking out upon the lake! The cabin faces west over the lake so it's a wonderful spot to watch the sun set!

Guest favourite
A cottage with a white exterior is set amidst trees with bare branches, indicating a winter landscape. A gravel path leads to the entrance, and a small porch is visible at the front. Snow lightly dusts the roof, enhancing the serene ambiance.
Cabin in Hinsdale
4.92 out of 5 average rating, 111 reviews

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage

Guest favourite
A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.
Home in Pittsfield
4.98 out of 5 average rating, 134 reviews

Hidden Oasis in the Mountains by Evergreen Home

7 MINUTES TO BOUSQUET MOUNTAIN Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

Top guest favourite
A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.
Cottage in Great Barrington
4.93 out of 5 average rating, 319 reviews

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

Popular amenities for rentals with a hot tub in Pittsfield

Quick stats about holiday rentals with a hot tub in Pittsfield

  • Total holiday rentals

    Explore 10 holiday rentals in Pittsfield

  • Nightly prices starting at

    Pittsfield holiday rentals start at £91 per night before taxes and fees

  • Verified guest reviews

    Over 770 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Pittsfield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Pittsfield rentals

  • 4.9 Average rating

    Pittsfield stays are highly rated by guests – averaging 4.9 out of 5!

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