
Holiday houses in Pittstown
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Top-rated holiday rentals in Pittstown
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#2 at Grafton Inn
Welcome to the historic Grafton Inn. #2 has been remodeled in the former block of Motel rooms, this apartment offers one bedroom a fold out in the living room and 1.5 bath. 5 acre property touches Grafton Lakes State Park, is 5 minute from the beach, and has pond and short nature trail. Also 2 miles from Grafton Peace Pagoda. 24 min to Troy, NY. 28min to Bennington, VT. 25 min to Williamstown, MA. Additional Listings on same property: airbnb.com/h/graftoninn4 airbnb.com/h/graftoninn3

Birch House - lake, green trees + modern comforts
We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

The Hygge Loft- mid-mod cabin on 70 acres w/HotTub
The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Grey House
Nestled in the beautiful hills of Grafton New York Greyhouse welcomes you. Grey house is a one story home that has been completely renovated with your comfort in mind. Adjacent to Greywacke Meadows. The 3 bedrooms are attractive and comfortable and sleep up-to six guests. Master bedroom has a private bathroom and a main bathroom is centrally located. Not wheelchair accessible at this time as there are stairs into the house. Multi level porches and a large patio with seating areas.

The Vermont Farmhouse|Hiking|Dog Trails|Village
Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Tranquil Retreat for Horse Lovers
Set on 38 acres, the home is influenced by Irish equestrians. Its owner Kelli spent time learning from some of the best horseman in Ireland who resided in their own “Hunt Box”or small living quarters connected directly to the barn. The large floor to ceiling windows allow you to experience watching the horses in their natural state. The space provides guests with the small, simple and beautiful moments of being an equestrian. This is an unforgettable experience like no other.

Exceptionally beautiful, spacious country home
The beautiful Sunburst house, which dates to the 1870s, has been fully modernized while still retaining its exceptional architectural details. The rooms are spacious, cozy and inviting and contain a charming mix of contemporary and antique furniture and decorations. Surrounded by multiple barns and 200 acres of fields and woods, the views from the hillsides behind the house are outstanding. Guests will enjoy the privacy and peace of living close to nature.

Cozy Retreat in the Trees
Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

Schoolhouse Spa Retreat on a Vermont Farm
Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Overlook at Graceful Acres Farmstay
Enjoy the grace of a historic family farm in the heart of eastern NY. Let the cool, fresh air and sounds of the outdoors start your day. Fill your time with a hike across our 440 acre farm then spend time with the animals and learn more about regenerative farming during a scheduled farm tour. Graceful Acres Farmstay is situated an hour south of the Adirondack State Park and within 35 minutes of Saratoga Springs, Albany, Troy, NY and Bennington, VT.

Riverfront Cabin • Heated Pool, Hot Tub & Sauna
Welcome to our COZY RIVERFRONT CABIN! This 3-bedroom, 2-bath escape sits right on the water and sleeps up to 8. LOADED with amenities! Enjoy a cedar wood sauna, custom wood-burning hot tub, private movie theater, a crackling fire pit, riverside hammock, and a fishing dock overlooking the river. Discover the unique specialties that every season has to offer with family and friends to unwind, reconnect, and soak in peaceful, unforgettable moments.

Unique Log Cabin on the Hudson-Minutes to Saratoga
This spacious, rustic, custom log cabin has everything you need for the perfect getaway. Large gas fireplace, custom furnishings, smart TVs in each bedroom, upgraded WiFi, new municipal water. Ping pong table, indoor shuffle board and corn hole in the basement area! Outdoors there are 4 kayaks for your use, a fire pit and bocce balls. Phenomenal fishing at the shoreline or from a kayak. Largemouth Bass, Striped Bass, Smallmouth Bass and more!
Popular amenities for Pittstown holiday rentals
Other great holiday rentals in Pittstown

1865 Farmhouse: mountain, monument & meadow views

Upstate Homestead Cottage

Mountain View Glamping. Off-Grid & Dog Friendly

Historic Stone Church in The Berkshires

Historic Cottage • 140-Year Pool Table & Garden

Summer Mountain Retreat + Views, Fire Pit, Hot Tub

A Hidden Sparrow

The Greylock Cabin
Destinations to explore
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- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Howe Caverns
- Six Flags Great Escape Lodge & Indoor Water park
- Butternut Ski Area and Tubing Center
- June Farms
- West Mountain Ski Resort
- Taconic State Park
- Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Naumkeag
- Norman Rockwell Museum





