
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 1,611 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!
FamilyLocationHiking

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
LocationFamilyView

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!
FamilyValueSkiing

Updated large condo across from AT and skiing
Family friendly, large 3 bedroom condo across the street from hiking and skiing in Killington. WiFi, cable TV, large gathering areas, spacious bedrooms, updated kitchen, and unlimited free firewood in winter. Plenty of après-ski chic touches make this a stylish yet comfortable retreat. 2 minute drive to Pico, 2 min walk to Appalachian Trail! Whether skiing, hiking, playing tennis, swimming, or game nights and cooking at-home meals with friends, this updated condo is a perfect spot to get away.
FamilyValuePool

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.
LocationIndoor spacesAccuracy

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…
FamilyLocationHeating

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!
LocationFamilyKitchen

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
FamilyLocationLong stay

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!
LocationValueCondition

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.
FamilyLocationAmenities

Snowcub- AC, Pool, Hot tub, Tennis, Grill!
Your group will be close to everything when you stay at this centrally-located condo. Enjoy two bedrooms plus a loft for a variety of sleeping options. Condo amenities include pool, gym, spa, tennis and hot tub. You will be close to the bars, restaurants, market and coffee shops and just minutes to the Killington resort base areas.
FamilyValueParking

Ranch at Mendon Mt Orchards
Cozy ranch house in an historic working apple orchard. Located on RT 4 in Mendon, we are just 6 miles from Pico and 11 miles from Killington ski areas. Great restaurants are just 3 miles down the road in Rutland. Shop in our store and bakery, stroll our orchard and visit the chickens, all while enjoying some spectacular views.
LocationFamilyGrill
Popular amenities for Pomfret rentals with a pool
House rentals with a pool

Ski Mountain View Estate
FamilyValueWifi

Golf and Mountain Biking outside the door!
ValueLocationDecor

Charming Sugarbush Standalone Condo
ValueLocationWifi

Classic VT Ski Chalet - Walkable to Okemo Ski Lift
ValueFamilyAir conditioning

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
ValueFamilyAccess

Woodstock retreat | 25 acres | private pond | spa
LocationCleanlinessComfort

The Wheelock House- Family Home in Quechee
FamilyLocationSleep quality

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

Mtn Green Condo-Ski/Bike Lifts, Covered Parking
ValueLocationBiking

Bright & Cozy Ski-in Condo with Mountain View
FamilyLocationAccess

Vermont Retreat, Dogs Welcome, Pool & Spa
ValueFamilyAccess

PeeP Hike Golf with Pool and Tennis 2 Bed on Mtn
FamilyValueBathroom

#45 Luxury Ski & Summer Condo with Private Sauna
FamilyValueAccuracy

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

Amazing,Ski, Golf, Hike, Bike, Adventures
FamilyLocationCleanliness

Cozy Mountain Retreat w Views | Pool, Hot Tub, Ski
ValueLocationPool
Other vacation rentals with a pool

2BR | Full Kitchen | River Access | Woodstock
LocationAmenities

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

Cozy Studio Apartment
FamilyLocationBackyard

Cozy Cabin - Lake, Ski, Golf!
FamilyLocationPool

Honeycrisp Cabin
LocationFamilyHot tub

New Resort Condo Close to Lifts
LocationFamilyCondition

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

Expansive dog friendly lakeview rental at Eastman
LocationFamilyComfort
When is the best time to visit Pomfret?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 5,189 ZAR | R 5,688 ZAR | R 4,496 ZAR | R 3,078 ZAR | R 4,351 ZAR | R 4,093 ZAR | R 3,432 ZAR | R 2,836 ZAR | R 3,497 ZAR | R 3,964 ZAR | R 4,480 ZAR | R 4,721 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 beach access Pomfret
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- Family-friendly rentals Pomfret
- House rentals Pomfret
- Rentals with a hot tub Pomfret
- 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
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Middlebury College
- Hildene, The Lincoln Family Home
- Killington Resort
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Ice Castles
- Squam Lakes Natural Science Center
- Stinson Lake
- Mount Sunapee Resort
- Montshire Museum of Science
- Warren Falls
- Camp Plymouth State Park





