
Vacation rentals with a pool in Pomfret
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Pomfret

Total vacation rentals
Explore 50 vacation rentals in Pomfret

Nightly prices starting at
Pomfret vacation rentals start at R 1,617 ZAR per night before taxes and fees

Verified guest reviews
Over 1,050 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
50 of Pomfret vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pomfret rentals

4.8 Average rating
Pomfret stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Pomfret
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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!

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!

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!

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…

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.

Ski Mountain View Estate
Pool is open for the summer of '26 Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Great multi family getaway

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!

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)
Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.

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.

Golf and Mountain Biking outside the door!
Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

Beautiful Spacious Condo at Killington Resort
This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

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.
Popular amenities for Pomfret rentals with a pool
House rentals with a pool

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Charming Sugarbush Standalone Condo

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

The Wheelock House- Family Home in Quechee

Fun in VT, Cozy and Comfy

Luxurious family retreat home in the mountains

Dana Road House Sunlit VT Country Home w/HotTub

Premier Quechee Newton Village Condo: Pet Friendly
Condo rentals with a pool

Serene Top Floor Condo (resort style amenities)

Bright & Cozy Ski-in Condo with Mountain View

#45 Luxury Ski & Summer Condo with Private Sauna

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

Amazing,Ski, Golf, Hike, Bike, Adventures

Updated large condo across from AT and skiing

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Cozy Condo- Close to Mountain, Ski home trail
Other vacation rentals with a pool

Luxury Container Home with Sauna & Heated Pool

Expansive dog friendly lakeview rental at Eastman

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

Relax&Play @ Tamarack House- Golf, Ski, Lake, Hike

Cozy Studio Apartment

Cozy Cabin - Lake, Ski, Golf!

Sunrise Bear Ridge: 4BR, 3BA Ski In/Ski Out Condo

The Chillington at Sunrise (ski in/out)
When is the best time to visit Pomfret?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 5,207 ZAR | R 5,708 ZAR | R 4,511 ZAR | R 3,088 ZAR | R 4,366 ZAR | R 4,107 ZAR | R 3,444 ZAR | R 2,846 ZAR | R 3,509 ZAR | R 3,978 ZAR | R 4,495 ZAR | R 4,738 ZAR |
| Avg. temp | -8°C | -7°C | -1°C | 6°C | 13°C | 18°C | 20°C | 19°C | 15°C | 8°C | 2°C | -5°C |
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- Rentals with pools Windsor County
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- Rentals with pools United States
- White Mountain National Forest
- Okemo Mountain Resort
- Squam Lake
- Stratton Mountain
- Sugarbush Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Middlebury College
- Killington Resort
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Ice Castles
- Squam Lakes Natural Science Center
- Stinson Lake
- Montshire Museum of Science
- Mount Sunapee Resort
- Warren Falls
- Camp Plymouth State Park





