Vacation rentals with a pool in Pomfret

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

Value · Family · Getting around

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!

Family · Location · Grill

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.

Value · Family · Indoor spaces

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.

Location · Parking · Getting around

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…

Value · Family · Kitchen

The Wheelock House- Family Home in Quechee

The Wheelock House is the ideal Quechee escape! Easy access to all Quechee and the Upper Valley has to offer. Under a mile to the club & ski hill, the location makes vacationing here a dream. In fall, pick apples at the orchard on our road. In winter, you can pop back-and-forth to the ski hill with ease, or snowshoe right out the back door on the green belt trails. In summer, enjoy two world-class golf courses, the lake, and beautiful rivers. Easy access to Dartmouth, Woodstock, & ski resorts.

Family · Location · Layout

Premier Quechee Newton Village Condo: Pet Friendly

Welcome to our Quechee Condo. We are a Colorado family with roots in New England and wanted our kids to grow up and experience the best of what New England has to offer. Quechee! This well cared for 3 bedroom unit is located near Lake Pinneo, the Quechee Clubhouse, Tennis/Pickle, Ski hill and Golf Courses. The condo comfortably sleeps 6 guests with an additional pull out sofa for more capacity. Close to Woodstock, Dartmouth, Killington & Okemo Golf, tennis, & Ski Hill are open to renters

Location · Family · Heating

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

Family · Location · TV

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.

Location · Family · Comfort

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.

Location · Hospitality · Sleep quality

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.

Location · Family · Pool

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.

Location · Family · Nearby