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Vacation rentals with a hot tub in Pittsfield

Find and book unique hot tub rentals on Airbnb

Quick stats about vacation rentals with a hot tub in Pittsfield

  • Total vacation rentals

    Explore 10 vacation rentals in Pittsfield

  • Nightly prices starting at

    Pittsfield vacation rentals start at G$31,381 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Pittsfield vacation rentals include wi-fi 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!

Top-rated hot tub rentals in Pittsfield

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

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Guest favorite
Chalet in Killington

Killington Chalet, Hot Tub, Sauna, Huge Boot Dryer

The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

Outdoor spacesHot tubAir conditioning

4.84 out of 5 average rating, 264 reviews
Superhost
Treehouse in Stockbridge

Romantic Treehouse- AC, PVT Hot tub, 20 Min to KLT

This unique treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows and custom bathroom/kitchen. My grandparents once owned and operated a dairy farm on the land. I want to share the treehouse and surrounding area with my guests. Located on the historic Rt 100 ski highway with easy access to Killington/Pico (20 min), Sugarbush (40 min) & Okemo (45 min). Private salt water hot tub directly under treehouse, new in 2026!

BathroomHot tubAmenities

4.9 out of 5 average rating, 157 reviews
Guest favorite
A vibrant autumn landscape is visible, featuring a two-story green townhome bordered by a well-maintained lawn. Colorful foliage on nearby trees and surrounding hills creates a warm ambiance, highlighting the natural beauty of the area in this scenic outdoor view.
Townhouse in Killington

Topridge 3BR w Incredible View & Private Hot Tub!

Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!

Hot tubOutdoor spacesAmenities

4.93 out of 5 average rating, 113 reviews
Guest favorite
A bright dining area is highlighted by a large wooden table, surrounded by black chairs. Natural light floods the space through multiple windows, accentuating the warm wooden beams above. A chandelier adds a touch of elegance, complementing the simple decor.
Home in Killington

Atelier Killington, hottub and amazing location

Welcome to Atelier in Killington, walking distance to shops and restaurants, yet situated in one the most private and enchanting settings in all of Killington. Surrounded by forest and a private reflective pond, foot bridges and cleared paths leading to expanses of protected land. Experience the fall colors or snow covered trees from the brand new pondside hottub. Experience Hygge to its fullest by having hot chocolate by the wood burning fireplace or fondue at our dining table that seats 10.

Outdoor spacesBathroomParking

4.92 out of 5 average rating, 170 reviews
Top guest favorite
An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.
Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

🚲 15 MINUTES to KILLINGTON 🛀🏼 PRIVATE HOT TUB 🔥 OUTDOOR SAUNA 🎥 Outdoor MOVIE PROJECTOR 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🐕 PET FRIENDLY 🏌️‍♂️ 15 MINUTES to GOLF 🥾 Close to HIKING 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. See below! 👰🏻 < 20 minutes to MOUNTAINTOP 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens

BathroomOutdoor spacesIndoor spaces

5.0 out of 5 average rating, 107 reviews
Top guest favorite
Chalet in Killington

The Overlook - Views | Hot Tub | Fire Pits | Games

Escape to stunning mountain views at The Overlook. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

BathroomHot tubSkiing

4.97 out of 5 average rating, 109 reviews
Guest favorite
A luxurious hot tub is positioned on a deck, offering stunning views of the distant mountains and lush greenery. The clear blue water is illuminated by natural light, enhancing the inviting space perfect for relaxation.
Home in Killington

BearWatch AC Hot Tub, Games, Grill, FirePit, VIEWS

Nestled in central Killington, this newly-renovated 5-bedroom gem boasts unmatched slope views on all floors. Enjoy two opulent king suites—one with a deck, the other with panoramic windows. Three additional cozy bedrooms, a state-of-the-art kitchen, original Killington bar, and a game room await. Outside, relish a unique hot tub, Weber BBQ, and a fire pit in a spacious yard. Walk to the shuttle, restaurants, bars, and markets. Tesla charger on-site. Dive into unparalleled luxury!

Hot tubOutdoor spacesKitchen

4.92 out of 5 average rating, 131 reviews
Top guest favorite
Tiny home in Ludlow

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Outdoor spacesBathroomCondition

4.96 out of 5 average rating, 115 reviews
Guest favorite
An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.
Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Hot tubOutdoor spacesCheck-in

4.87 out of 5 average rating, 173 reviews
Top guest favorite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Hot tubOutdoor spacesTV

4.99 out of 5 average rating, 330 reviews
Top guest favorite
A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.
Condo in Killington

AC, Vermont Retreat, Dogs Welcome, Pool & Spa

Coffee on the patio. Mountains turning gold. Your dog already halfway down the trail. That’s summer and fall at The Woods. This spacious dog-friendly 2BR sleeps 6 and features a full kitchen, fireplace, private patio, and access to the indoor pool, hot tub, and spa. Minutes from Killington Bike Park, hiking, golf, and restaurants, it’s the perfect home base for Vermont adventures. Bring the crew. Bring the pup. This is the place guests rebook before checkout.

Outdoor spacesHot tubComfort

4.94 out of 5 average rating, 306 reviews
Guest favorite
A cozy living space is highlighted by a modern pink chair positioned near a wood stove, which emits a warm glow. Large glass doors offer views of the wooded surroundings, while a Moroccan rug adds texture to the concrete floor.
Chalet in Royalton

Scandinavian design Chalet hiking trail + hot tub

This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.

Hot tubOutdoor spacesHospitality

4.94 out of 5 average rating, 226 reviews

Popular amenities for Pittsfield hot tub rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a hot tub

Guest favorite
The exterior of a three-level wooden house features a deep orange siding with large windows and a steep metal roof. A spacious wooden deck extends across the front, offering a natural, wooded backdrop. Surrounding landscaping includes a gravel path leading to the entrance.
Home in Killington

Cozy Private House on Killington Mtn - Hottub

Outdoor spacesBathroomAccuracy

4.94 out of 5 average rating, 127 reviews
Guest favorite
A cozy living room features a stone fireplace at its center, surrounded by natural wood paneling. Two red accent chairs are positioned beside a window, while a large gray sofa and green armchair offer ample seating. A coffee table rests in front, adorned with a textured blanket.
Home in Killington

Brookview Lodge, Killington, VT

BathroomHot tubBackyard

4.89 out of 5 average rating, 106 reviews
Top guest favorite
Home in Killington

Golf and Mountain Biking outside the door!

Hot tubOutdoor spacesView

4.89 out of 5 average rating, 139 reviews
Top guest favorite
A new hot tub with jets is positioned under a wooden structure, surrounded by grass and landscaped areas. A tranquil view of distant mountains and trees is visible in the background, creating a peaceful outdoor setting.
Home in Rutland

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

BathroomHot tubCheckout

4.9 out of 5 average rating, 245 reviews
Top guest favorite
A spacious living area features a modern wood-burning fireplace framed by light brick, with a mounted flat-screen TV above. Comfortable grey sofas and a wooden coffee table are arranged to encourage relaxation, while a wooden staircase leads to the upper level.
Home in Hartford

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Hot tubOutdoor spacesLayout

4.96 out of 5 average rating, 178 reviews
Top guest favorite
The rustic exterior of Kendall Brook Lodge is displayed, featuring a large deck with several Adirondack chairs. A Nordic hot tub is prominently visible, surrounded by a backdrop of trees showcasing autumn foliage. The wooden structure is complemented by large windows allowing natural light.
Home in Granville

Kendall Brook Lodge

BathroomOutdoor spacesAccess

4.96 out of 5 average rating, 115 reviews
Top guest favorite
A spacious living area features large windows allowing natural light to fill the room. A gray sofa with decorative pillows is centered on a decorative area rug. The open layout connects to the kitchen and dining area, enhancing the inviting atmosphere.
Home in Salisbury

Lake Dunmore Retreat 15 min to Middlebury College

BathroomHot tubHiking

4.96 out of 5 average rating, 146 reviews
Top guest favorite
Home in Tunbridge

Town’s End, a Private Retreat with Mountain Views

BathroomHot tubAccuracy

4.94 out of 5 average rating, 119 reviews

Villa rentals with a hot tub

Top guest favorite
The unique house features a modern design with large glass windows allowing for natural light. It is surrounded by lush greenery, with a wooden deck visible on the upper level. Trees and foliage provide a serene, private setting.
Villa in Ludlow

Modern 3 Bedroom 4 Bath Villa w HotTub/ back trail

BathroomHot tubComfort

4.93 out of 5 average rating, 57 reviewsAn indoor swimming pool area is illuminated by natural light filtering through high windows. The spacious pool features clear blue water, while a hot tub is situated nearby. The room showcases a modern design with wooden beams and tiled flooring.
Villa in Killington

Base of Killington with Sports center access Golf

Hot tubComfortKitchen

4.69 out of 5 average rating, 13 reviews
Guest favorite
A comfortable living area features a gray sectional sofa and a pull-out sofa bed, positioned beside a circular coffee table. Large windows with sheer curtains allow natural light into the space, while a wooden ceiling adds warmth. A small fireplace and bear-themed wall art enhance the ambiance.
Villa in Killington

Base of Killington with Sports center, golf

WalkabilitySkiingAmenities

4.83 out of 5 average rating, 6 reviews
Villa in Killington

Sunrise East Glade C8 Ski on Ski off

Hot tubLocationCheck-in

4.75 out of 5 average rating, 4 reviewsA spacious living area is centered around a stone fireplace, complemented by a wooden ceiling. Two armchairs and a sofa provide comfortable seating, while a coffee table occupies the center. Natural light enters through a large window, offering a view of the outdoors.
Villa in Killington

Base of Killington with Sports center access Golf

BathroomAccessLocation

4.67 out of 5 average rating, 3 reviewsA comfortable living area is featured, showcasing a soft beige couch and a light gray armchair positioned around a wooden coffee table. Natural light filters through large windows, highlighting the wooden ceiling and creating a cozy ambiance.
Villa in Killington

Base of Killington with Sports center access Golf

Hot tubCleanlinessIndoor spaces

4.6 out of 5 average rating, 5 reviewsA comfortable living area is featured, showcasing a spacious sofa and an armchair. A wooden coffee table sits at the center, with a TV mounted on the wall opposite. Natural light streams in through a window, complemented by warm lighting from wall sconces.
Villa in Killington

Base of Killington with Sports center access Golf

Hot tubHospitalityKitchen

A comfortable living space features two armchairs and a spacious sofa, arranged around a central coffee table. Natural light pours in through large windows adorned with soft drapes, and a cozy wood-burning fireplace is framed by a wooden mantel.
Villa in Killington

Base of Killington with Sports center access Golf

AccuracyLocation

Cabin rentals with a hot tub

Top guest favorite
A peaceful scene is depicted, showcasing vibrant autumn foliage reflected in the calm waters of a small pond. The rustic cabin is nestled among the trees in the background, complemented by a canoe resting at the water's edge.
Cabin in Bethel

Rustic and Cozy Vermont Getaway at Sugarwood Cabin

BathroomOutdoor spacesLong stay

4.93 out of 5 average rating, 564 reviews
Guest favorite
A rustic cabin is nestled among the trees, showcasing its wooden exterior and a metal roof. Tall windows allow natural light to fill the space. Surrounding greenery, including ferns and bushes, adds to the secluded atmosphere. A stone wall and picnic table can be seen in front.
Cabin in Sharon

forest retreat; off-grid writers cabin

Hot tubOutdoor spacesHiking

4.93 out of 5 average rating, 302 reviews
Guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Outdoor spacesBathroomCheck-in

4.95 out of 5 average rating, 267 reviews
Guest favorite
The cabin entrance is framed by freshly fallen snow, with wooden siding that blends into the winter landscape. A lantern on the left provides a soft glow, illuminating the path. Tranquil trees surround the area, enhancing the serene atmosphere.
Cabin in Plymouth

~The ClubHaus~

BathroomOutdoor spacesAccess

4.99 out of 5 average rating, 131 reviews
Guest favorite
Cabin in Cavendish

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Hot tubBathroomNearby

4.96 out of 5 average rating, 114 reviews
Guest favorite
Cabin in Winhall

A frame cabin with Hot tub near Stratton, VT

Hot tubBathroomTV

4.91 out of 5 average rating, 126 reviews
Top guest favorite
The rustic cabin sits amidst a lush green landscape, framed by towering trees. The stone chimney adds character, while the two separate structures showcase a combination of wood siding and modern roofing. Clear blue skies create a serene backdrop for the natural beauty.
Cabin in Landgrove

The Owl’s Nest in Landgrove

Hot tubBathroomFamily

4.99 out of 5 average rating, 220 reviews
Superhost
Cabin in Londonderry

Stunning Rustic Apple Barn - hot tub & sauna

Hot tubBathroomCondition

4.81 out of 5 average rating, 510 reviews

Destinations to explore