Holiday rentals with a hot tub in Pittsfield

Find and book unique hot tub accommodation on Airbnb

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 $210 AUD per night before taxes and fees
Verified guest reviews
Over 1,170 verified reviews to help you choose
Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 of Pittsfield holiday 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 accommodation in Pittsfield

Guests agree: These hot tub accommodation options are highly rated for location, cleanliness and more.

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Guest favourite

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!

BathroomOutdoor spacesNearby

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!

Outdoor spacesHot tubQuiet

4.9 out of 5 average rating, 157 reviews

Guest favourite

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!

BathroomHot tubAccess

4.93 out of 5 average rating, 113 reviews

Guest favourite

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.

BathroomHot tubComfort

4.92 out of 5 average rating, 170 reviews

Top Guest favourite

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

BathroomHot tubSleep quality

5.0 out of 5 average rating, 107 reviews

Top Guest favourite

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

Outdoor spacesBathroomCheckout

4.97 out of 5 average rating, 109 reviews

Guest favourite

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!

Outdoor spacesHot tubHeating

4.92 out of 5 average rating, 131 reviews

Top Guest favourite

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 spacesBathroomGetting around

4.96 out of 5 average rating, 115 reviews

Guest favourite

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.

BathroomOutdoor spacesHiking

4.87 out of 5 average rating, 173 reviews

Top Guest favourite

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*

Outdoor spacesBathroomWi-Fi

4.99 out of 5 average rating, 331 reviews

Top Guest favourite

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.

Hot tubBathroomCheckout

4.94 out of 5 average rating, 306 reviews

Guest favourite

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.

Outdoor spacesBathroomHeating

4.94 out of 5 average rating, 226 reviews