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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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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!

FamilyLocationGetting around

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

FamilyValueCondition

4.92 out of 5 average rating, 61 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 Foliage Views & 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!

ValueLocationLayout

4.93 out of 5 average rating, 115 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!

LocationValueSkiing

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.

LocationQuietComfort

4.98 out of 5 average rating, 40 reviews
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

Come relax at our cozy retreat after a day of skiing or golf. 36 challenging holes or Ski-in/out from your door. Sweeping mountain views, vaulted ceilings, huge sleeping loft & fireplace, this open concept home is a great escape for couples/families. Strong Wi-Fi & dedicated office space make it easy for distance working. 4 smart TVs & plenty of games/toys for relaxing at home too! Plus our guests have access to all Quechee Resort amenities like gym/sauna/pools/beach/racquet/dining & more…

FamilyValueBathroom

4.88 out of 5 average rating, 85 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

ValueLocationAir conditioning

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.

FamilyLocationGetting around

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.

LocationAmenities

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!

ValueFamilySkiing

4.79 out of 5 average rating, 337 reviews
Top guest favorite
A cozy living area is visible, featuring a dining table surrounded by bright yellow chairs. A fireplace is seen, enhancing the space, while a large bear-themed wall mural adds a touch of nature. Natural light floods in from the nearby window.
Condo in Killington

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer.

ValueFamilyPool

4.93 out of 5 average rating, 247 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.

LocationFamilyCheck-in

5.0 out of 5 average rating, 17 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

LocationFamilyAmenities

4.96 out of 5 average rating, 142 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

ValueFamilyGetting around

4.9 out of 5 average rating, 184 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

FamilyValueBiking

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

Golf and Mountain Biking outside the door!

ValueLocationHeating

4.89 out of 5 average rating, 141 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

LocationValueComfort

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

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

LocationValueHot tub

4.92 out of 5 average rating, 172 reviews
Guest favorite
An aerial view captures a tranquil backyard featuring a private in-ground pool surrounded by a stone patio. The farmhouse is visible in the background, framed by trees and open lawn space. A shaded seating area and hammock provide relaxation options.
Home in Hartland

Private Farmhouse with in ground pool!

ValueLocationHeating

5.0 out of 5 average rating, 22 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

LocationFamilyWifi

5.0 out of 5 average rating, 26 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

ValueLocationWalkability

4.91 out of 5 average rating, 110 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

FamilyValueCleanliness

4.84 out of 5 average rating, 188 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

FamilyValueWalkability

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

LocationFamilyDecor

4.87 out of 5 average rating, 127 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

ValueFamilyHot tub

4.94 out of 5 average rating, 112 reviews
Guest favorite
Condo in Killington

Luxe Trailside Ski + Bike On/Off. Next to hot tub

LocationValueAmenities

4.89 out of 5 average rating, 104 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

FamilyLocationShared spaces

4.8 out of 5 average rating, 116 reviews
Top guest favorite
A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.
Condo in Killington

Newly renovated ski retreat at Killington

ValueLocationView

4.94 out of 5 average rating, 232 reviews

Other vacation rentals with a pool

Guest favorite
Apartment in Killington

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

FamilyLocationSkiing

4.93 out of 5 average rating, 29 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!

FamilyLocationHospitality

4.98 out of 5 average rating, 56 reviews
Guest favorite
Apartment in Killington

Killington Sapphire

LocationValueSkiing

5.0 out of 5 average rating, 7 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

FamilyLocationAmenities

4.99 out of 5 average rating, 98 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

FamilyValueAmenities

4.98 out of 5 average rating, 45 reviews
Top guest favorite
A relaxing hot tub overlooks the in-ground swimming pool, surrounded by vibrant greenery and landscaped gardens. A gazebo is positioned nearby, with mountains visible in the distance, creating a serene outdoor environment suitable for leisure and gatherings.
Home in Dorset

Idyllic Dorset Home: Serene Escape w/amazing views

LocationFamilyView

4.98 out of 5 average rating, 42 reviews
Guest favorite
A welcoming living area features a comfortable gray sofa with red accent pillows, a round braided rug, and a decorative wooden coffee table. A gas fireplace is set against a brick wall, accompanied by large windows offering views of the outdoors. A TV sits on a light wooden stand, complementing the overall rustic charm.
Townhouse in Eastman

Expansive dog friendly lakeview rental at Eastman

LocationFamilySkiing

4.93 out of 5 average rating, 58 reviews
Guest favorite
A bright living area is filled with natural light from large windows, showcasing views of the outside. Soft, orange sofas and a wooden coffee table are arranged on a plush area rug, while a telescope stands by the window for observing the landscape.
Home in Mendon

Jam House:Renovated Luxury+Pool+Land+Hot Tub+Sauna

FamilyValueParking

4.93 out of 5 average rating, 60 reviews

Destinations to explore