Vacation rentals with a hot tub in Windsor County

Find and book unique hot tub rentals on Airbnb

Top-rated hot tub rentals in Windsor County

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

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Superhost

Home in South Londonderry

4.86 out of 5 average rating, 152 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!!

Guest favorite

Chalet in Stockbridge

4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile mountain biking trails. This 3 bedroom, 2 bath upper unit duplex. with outdoor private Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events Fantastic unit check our reviews

Guest favorite

Tiny home in Clarendon

4.9 out of 5 average rating, 226 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Guest favorite

Home in Rutland

4.89 out of 5 average rating, 184 reviews

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

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mountain views, peaceful brook on 1+ acre property. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV.

Top guest favorite

Home in Killington

4.99 out of 5 average rating, 145 reviews

DoubleDen - AC, Hot Tub, Game Room, Fire Pit

Fantastic location on Killington Road! This interior connected duplex, offered as the entire house with 6 bedrooms, 4 baths is located at the shuttle stop, and a few minutes from the main resort base. Walk to some of the best restaurants and night clubs. Relax in large outdoor hot tub, or play with the arcade games, foosball, or pool table. Enjoy fast internet over the gigabit connection on the 75" TV (or one of several others), or go retro with the 80's VHS and console game areas downstairs.

Top guest favorite

Home in Ludlow

4.97 out of 5 average rating, 158 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Newly renovated in fall 2023, this 3-level, 1700+ sq. ft. ski chalet is just a 4 min drive to Okemo Mountain Resort and town, with Jackson Gore only 6 min away. Floor-to-ceiling windows showcase stunning 180-degree views of the wooded backyard, creating a peaceful mountain retreat. Cozy up by the fireplace or soak in the Jacuzzi hot tub for ultimate relaxation. Whether you're here for skiing, hiking, or a quiet escape, this private oasis offers the perfect blend of comfort and convenience.

Guest favorite

Tiny home in Chester

4.99 out of 5 average rating, 135 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Superhost

Home in Killington

4.78 out of 5 average rating, 9 reviews

Whitetail Chalet: Hot Tub | Close to Resort

Discounted Lift Tickets Available! Welcome to our mid-century modern chalet, perfect for a serene wooded mountain escape year-round. Recently renovated, this home offers all the comforts to make you feel right at home. Conveniently located, this fully renovated home accommodates up to eight guests in four bedrooms and two bathrooms. Enjoy modern amenities, including new appliances, fast and reliable WiFi, and two 55” HD televisions, and four person hot tub (fee may apply).

Top guest favorite

Cabin in Killington

4.97 out of 5 average rating, 30 reviews

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

This luxury residence on Killington Mountain is a 400-yard walk to the closest ski trail or a short 5-minute drive to the principal ski bases, along with the resort's array of bars, eateries, and retail outlets. It features an indoor jacuzzi, a spacious living/kitchen area bathed in natural light. A variety of summer pursuits, including golf, hiking, mountain biking, and canoeing, are conveniently accessible within minutes from the home. Plus, the property welcomes pets.

Guest favorite

Home in Plymouth

4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Superhost

Cabin in Mount Holly

4.86 out of 5 average rating, 125 reviews

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.

Guest favorite

Condo in Killington

4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).