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Vacation rentals with a pool in Ottauquechee River

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Top-rated rentals with a pool in Ottauquechee River

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost
Home in Killington

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

4.86 out of 5 average rating, 260 reviews
Guest favorite
The exterior of a newly renovated retreat showcases a wooden structure surrounded by trees. A fire pit is set with several dark chairs arranged in a circular formation. Soft light emanates from the large windows, providing a glimpse into the warm interior spaces.
Home in Bridgewater

Luxurious family retreat home in the mountains

An exquisite newly renovated country retreat nestled between the mountains on 30 acres. Pond, open pasture and woodlands to explore. Indoor infrared sauna with red light therapy. Spa bathroom with freestanding tub and two rain water showers. Organic bedding. Grand fireplace. Large open concept kitchen with top of the line appliances and 14 stage drinking water filter. Movie theater. Kids space. 3 bedrooms + loft Killington Skyship Gondola - 7 minutes Okemo - 25 minutes Woodstock - 20 minutes

4.92 out of 5 average rating, 61 reviews
Top guest favorite
A bright and airy great room features high wooden ceilings with large windows showcasing mountain views. A spacious sectional sofa is arranged around a colorful area rug, complemented by blue armchairs. Contemporary lighting and artistic decor add to the inviting ambiance.
Home in Springfield

Luxury Mid-Century Modern Vermont Home, Okemo View

The Brewster House is a premiere destination for skiing, hiking, enjoying the country or just lounging by the pool. Designed by renowned mid-century modern architect turned painter George W.W. Brewster, the Brewster House has been lovingly restored and updated, and filled with original, local art. With gorgeous views of Okemo and Hawks Mountain Wildlife Area, the Brewster House is close to incredible dining, great art galleries, and antique shops. Come bask in beauty and relax completely!

4.99 out of 5 average rating, 101 reviews
Top guest favorite
Guesthouse in Pomfret

Cozy, clean studio with picturesque Vermont views!

Lovely studio in the heart of the mountains! Our cozy and well-lit space is perfect for solo travelers or couples looking to explore all that Vermont has to offer. Enjoy a queen-sized bed, pull out sofa, kitchenette and a charming bathroom, plus a beautiful new stone patio for relaxing outdoors. 2 miles to Woodstock and 1 mile to Saskadena Six. Experience local life with all the modern amenities you need for a memorable stay. In the winter months, 4 wheel drive or all wheel drive is mandatory.

4.98 out of 5 average rating, 40 reviews
Top guest favorite
The charming yellow home is set against a backdrop of autumn foliage, showcasing green lawns and a wooden fence. A gazebo is visible nearby, inviting relaxation. The structure features a gabled roof and is oriented towards the scenic landscape.
Home in Woodstock

Dana Road House Sunlit VT Country Home w/HotTub

Dana Road House: an idyllic 3BR/2BA VT country home Ideally located just 1.7 miles from Woodstock Village & 20 min. to Killington Skyeship. Gazebo with cedar hot tub, patio with dining , chiminea & BBQ Spacious open floor plan, chef's kitchen, 2 living areas, wood stove, Smart TV & WiFi. 3 comfortable bedrooms: a king master suite with jetted tub, queen room with brass bed and a double twin room. All amenities provided for your comfort & enjoyment. Follow on Social @DanaRoadHouse

4.97 out of 5 average rating, 73 reviews
Top guest favorite
Home in Hartford

Cozy Vermont Cabin | Near Woodstock + Quechee

Escape to Pine & Plaid, our Guest Favorite four-bedroom reimagined 1970's cabin in Quechee, Vermont. Tucked into the woods just minutes from Woodstock, it’s made for crisp fall weekends and cozy November getaways. Explore Quechee Gorge, hike nearby trails, browse Woodstock’s shops and restaurants, then come home to gather around the fire pit. Sleeps 8 with plenty of space for families and friends looking for a stylish, relaxed New England escape. Follow us @pineandplaidvt for more.

5.0 out of 5 average rating, 17 reviews
Superhost
Apartment in Woodstock

2BR | Full Kitchen | River Access | Woodstock

S'mores by the fire, little ones in the pool, and a fully equipped kitchen or on-site restaurant waiting when you need it — this is elevated family Inn living at On The River Inn. Just minutes from downtown Woodstock, our large ground floor apartment has a king bed, a full bed, shared outdoor seating, and direct access to 6 acres of gardens and river. Daily breakfast, afternoon cookies, game room, library, and toddler play room, gym, pool and sauna access all included.

4.75 out of 5 average rating, 4 reviews
Superhost
Home in Woodstock

Woodstock retreat | 25 acres | private pond | spa

25 private acres in Vermont's Green Mountains, just 5 minutes from downtown Woodstock's shops and restaurants — seclusion without the drive. Spend evenings by the spring-fed pond, soak in the hot tub, or unwind in the sunset rockers as the mountains change color. Inside, a spacious, modern great room brings the whole family together after a day exploring. Rare to find the ultimate privacy and proximity like this — most estates this quiet are an hour from anywhere.

4.75 out of 5 average rating, 4 reviews
Guest favorite
A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.
Condo in Killington

Serene Top Floor Condo (resort style amenities)

Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it!

4.79 out of 5 average rating, 337 reviews
Top guest favorite
Shipping container in Ludlow

Luxury Container Home Sauna-Heated Pool-Hot Tub

Escape to a luxury modern container retreat minutes from Okemo Mountain. Set on 3 private acres with mountain views, this unique getaway features a sauna, heated plunge pool and thoughtfully designed modern interiors. Perfect for skiing, hiking, fall foliage, or relaxing in nature, the home blends comfort, style, and privacy while still being close to restaurants, lakes, golf, and everything Ludlow has to offer year-round.

5.0 out of 5 average rating, 17 reviews
Top guest favorite
Condo in Killington

Ski-In/Out, Hot Tub, Pet-Friendly

Escape to a spacious, pet-friendly 1-bedroom mountain condo in Killington, comfortably sleeping 4. Enjoy year-round adventures with easy access to hiking, biking, golf, and skiing. The condo is 488 ft to the sunrise lift! Relax on your private balcony, by the gas fireplace, or at the resort's indoor/outdoor pools, hot tub, and fitness center. Perfect for a serene mountain getaway with all amenities.

4.95 out of 5 average rating, 182 reviews
Top guest favorite
Condo in Killington

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

Revel in this bright and modern ski condo just off Killington's main road and close to everything. Relax after a day on the mountain streaming on one of your 3 smart TVs. Indulge with the fabulous condo amenities including the pool, hot tubs, spa, gym, and tennis courts, or settle in by the wood-burning fire. Spread out in this spacious condo and enjoy all that Killington has to offer.

4.96 out of 5 average rating, 223 reviews

Popular amenities for Ottauquechee River rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Springfield

Ski Mountain View Estate

4.96 out of 5 average rating, 142 reviews
Superhost
The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.
Home in Mendon

Ranch at Mendon Mt Orchards

4.87 out of 5 average rating, 283 reviews
Guest favorite
Home in Killington

Golf and Mountain Biking outside the door!

4.89 out of 5 average rating, 141 reviews
Guest favorite
A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.
Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

4.9 out of 5 average rating, 184 reviews
Guest favorite
The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.
Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

4.92 out of 5 average rating, 114 reviews
Guest favorite
Home in Killington

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

4.92 out of 5 average rating, 172 reviews
Top guest favorite
A two-level house exterior showcases a wooden deck with seating, surrounded by trees. Large glass doors provide views of the outdoor space, while comfortable chairs are positioned on the deck. A gravel pathway leads to the entrance, enhancing the serene woodland setting.
Home in Hartford

Fun in VT, Cozy and Comfy

5.0 out of 5 average rating, 26 reviews
Top guest favorite
An open living and dining area is highlighted by large windows allowing natural light to fill the space. A wooden dining table with eight chairs is present, alongside a comfortable seating arrangement featuring a sofa and an accent chair. A glamor chandelier hangs overhead, enhancing the welcoming atmosphere.
Home in Hartford

Premier Quechee Newton Village Condo: Pet Friendly

4.94 out of 5 average rating, 63 reviews

Condo rentals with a pool

Guest favorite
A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.
Condo in Killington

Great PeeP rates Hike Golf Tennis 2 Bed on Mtn

4.91 out of 5 average rating, 110 reviews
Guest favorite
A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.
Condo in Killington

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

4.91 out of 5 average rating, 227 reviews
Guest favorite
Aerial view captures a large cluster of buildings nestled among vibrant autumn foliage, showcasing shades of orange, yellow, and green. Majestic mountains rise in the background, while a spacious parking area is visible, surrounded by trees.
Condo in Killington

Updated large condo across from AT and skiing

4.87 out of 5 average rating, 127 reviews
Superhost
A cozy living area features a brick fireplace at its center, surrounded by two comfortable armchairs and a wooden coffee table. A Roku Smart TV is positioned next to large glass doors leading to the balcony, while a mirror reflects the warm ambiance. Natural light enhances the wooden accents on the walls.
Condo in Killington

Cozy Condo- Close to Mountain, Ski home trail

4.84 out of 5 average rating, 188 reviews
Top guest favorite
The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.
Condo in Mendon

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

4.89 out of 5 average rating, 124 reviews
Top guest favorite
A spacious living room features a real wood fireplace with a modern hearth, surrounded by a cozy seating arrangement. A flat-screen television is mounted above the fireplace. Large windows provide natural light and a view of the outdoor balcony, enhancing the inviting atmosphere.
Condo in Killington

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

4.94 out of 5 average rating, 112 reviews
Guest favorite
The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.
Condo in Killington

Cozy Mountain Retreat w Views | Pool, Hot Tub, Ski

4.9 out of 5 average rating, 154 reviews
Superhost
The cozy living area features a stone fireplace and a 42" flat-screen TV mounted on the wall. Comfortable sofas are arranged around a wooden coffee table, with decorative pillows adding warmth to the space. Soft natural light enters through the nearby window, enhancing the inviting atmosphere.
Condo in Killington

Elegant 3BR Escape | Hiking & Nature Nearby

4.8 out of 5 average rating, 116 reviews

Other vacation rentals with a pool

Superhost
An inviting living area features comfortable sofas and an orange armchair. A wooden coffee table is positioned centrally, with a fireplace adorned by a brick wall as a focal point. Natural light streams in through large windows, illuminating the warm interior.
Townhouse in Hartford

Specials Ski-in Ski-Out Cozy Mountainside Condo

4.88 out of 5 average rating, 85 reviews
Guest favorite
Apartment in Killington

Skier's Retreat | Hot Tub | Sauna | Free Shuttle

4.93 out of 5 average rating, 29 reviews
Top guest favorite
A warm living area features a stone fireplace as the focal point, complemented by wooden beams and walls. A gray sofa and a red armchair invite relaxation, while a wooden coffee table holds a stack of magazines. Large windows allow natural light to fill the space.
Chalet in Ludlow

Five Bedroom Family Home on Okemo with A.C. splits

4.98 out of 5 average rating, 45 reviews
Top guest favorite
A cozy studio apartment showcases a wood-burning stove located on a brick hearth. A dark sofa is positioned across from a flat-screen TV mounted on the wall. The space is illuminated by sunlight through two windows, draped with sheer white curtains.
Apartment in Thetford

Cozy Studio Apartment

4.99 out of 5 average rating, 98 reviews
Top guest favorite
An open living area features high vaulted ceilings and large windows, allowing natural light to fill the space. A cozy leather couch is complemented by a light-colored ottoman. A dining table for six is positioned nearby, while a loft area can be seen above.
Cabin in Eastman

Cozy Cabin - Lake, Ski, Golf!

4.98 out of 5 average rating, 56 reviews
Guest favorite
A spacious living area is highlighted by a comfortable gray sofa and a wooden coffee table. Natural light streams through large windows, complementing the warm wood paneling that separates the sleeping nook. A flat-screen TV and a cozy seating arrangement add to the inviting ambiance.
Condo in Killington

Cozy Slopeside Studio at Pico

5.0 out of 5 average rating, 35 reviews
Top guest favorite
A cozy cabin with a wooden exterior sits in a grassy area surrounded by trees. Two red chairs are positioned on the porch, inviting relaxation. A picnic table and a fire pit with stone edging are located nearby, enhancing the outdoor setting.
Cabin in Brandon

Honeycrisp Cabin

4.96 out of 5 average rating, 52 reviews
Guest favorite
Apartment in Killington

Killington Sapphire

5.0 out of 5 average rating, 7 reviews

Destinations to explore