
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.

The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Walk to Mt. Snow-Spa-Summer Pool
*Exterior construction on siding until end of Feb *Amenity rich studio only a 5 min walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

Elegant Year-Round Lakeside Retreat with AC
The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

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!

Hidden Oasis in the Mountains by Evergreen Home
Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

HOT TUB! Spring Time! Berkshires! Dog-Friendly!
Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Patio w/ Hot tub, fire pit, canoe use -Acre wooded/secluded lot -Ski Otis Ridge 15 min or Butternut 30 min -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Naumkeag Lights -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch -Generator on site

Boutique TINY home+private HOT TUB-walk to Main St
Love month at Art Park. Romance is built in—no add-ons needed: Roses-Prosecco-Robes-Slippers. Boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful oasis just 2 mins from Chatham’s Main Street lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis at @artparkhomes.

Berkshire Mountain retreat with Urban eco-luxuries
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

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!

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

Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Winter Dream! The Handle Lodge at Snowtree Condos
The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.
Popular amenities for rentals with a hot tub in Pittsfield
House rentals with a hot tub

Escape to Lakefront Leisure—Amazing views!

Modern and cozy 3 bedroom with outdoor oasis

4Br Mountain Brook House on 130 acres w/ trails

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Art House! W Hot Tub By Mass Moca

Upstate Riverfront Getaway with Hot tub

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Walk To Town, Hottub, Firepit, Games, Mt Snow
Villa rentals with a hot tub
Magnificent Hudson River Estate with Infinity Pool and Spa

Vermont Vacation Villa—Grapevine Getaway

Spacious Villa with Access to Various Amenities!

Retreat to 56 Acres w/ Hot Tub, 2 Acre Pond, Pool

Villa with Access to Amazing Amenities!

Villa with Access to Various Amenities
Cabin rentals with a hot tub

Private Family Cabin 3.5ac • HotTub • Water Access

Modern cabin retreat

Secluded A-Frame Cabin: Hot tub, Views, EV charger

The Airstream at June Farms

Charming Lakefront Cabin with Hot Tub

The Red Cabin-Secluded Getaway with backyard Brook

Catskills Log Home, Stunning Mountain Views

Cozy Grove Luxury Cabin
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 £89 per night before taxes and fees

Verified guest reviews
Over 700 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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- Rentals with a hot tub Berkshire County
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- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Thacher State Park
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Ski Sundown
- Hildene, The Lincoln Family Home
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Poets' Walk Park
- Millbrook Vineyards & Winery




