Holiday rentals in Pittstown

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Top-rated holiday rentals in Pittstown

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Top guest favourite
The entrance to the guest house displays a dark wood-paneled exterior with a black door featuring a grid window. A small window is positioned beside the door. Recessed lighting illuminates the covered porch area above.
Guest house in North Bennington
4.99 out of 5 average rating, 329 reviews

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

Top guest favourite
A historic brick house is showcased, featuring two distinct sections with green shutters and a vibrant red door. Surrounding trees display autumn foliage in shades of orange and yellow. A well-maintained lawn and a pathway are visible in the foreground, enhancing the property's inviting curb appeal.
Flat in Clifton Park
4.98 out of 5 average rating, 110 reviews

The Old Canal House at Halfmoon

Located in a 200-year old historic brick house, the guest apartment is fully furnished and all windows face the Mohawk River and a scenic walk path. Nearby Kayak rental is available. We are located a few minutes’ drive from The Klam'er Tavern and Marina and about 30 minutes from Saratoga Springs and Albany, where art performances, concerts and dining experiences await you. At all times, you can enjoy the view on the river from your own private patio or the warmth of the fire pit in the yard.

Top guest favourite
A spacious family room features wooden walls and beams, with a comfortable couch and a coffee table in the foreground. A large TV is mounted on the wall, and a dining area is visible in the background, illuminated by natural light from windows framed by greenery.
Flat in Greenwich
4.95 out of 5 average rating, 121 reviews

Apartment in Historic Village Home

Our home was built in the 1830's, and the apartment added in the 1950's. The apartment has a throwback feel. We are an easy walk to restaurants, Flynn's funeral home, the school, and churches. We are minutes from the Washington County Fairgrounds. We are 1/2 an hour from the Saratoga race track, 45 minutes to Lake George, 10 minutes from Willard Mt, and an hour from great Vermont skiing! We have a full kitchen, guests say our beds are super comfy, and we have hi-speed cable and Internet!

Top guest favourite
Cottage in Valatie
4.99 out of 5 average rating, 149 reviews

Private Hudson Valley Lakefront-Kayak, SUP, Fish,

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the 8 miles of shoreline -Catch the sunset, then end the day sharing stories around the starlit firepit. An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Top guest favourite
A spacious living area features high vaulted ceilings with exposed wooden beams and large skylights. Natural light illuminates the modern decor, including a comfortable couch, sleek bar stools, and a central coffee table. A fireplace is positioned beside expansive windows that offer views of the surrounding forest.
Cabin in Shaftsbury
4.99 out of 5 average rating, 313 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

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!

Top guest favourite
The unique dome-shaped structure is composed of iron and cement, surrounded by lush greenery. Large windows create a bright and airy atmosphere, while the greenhouse-style addition at the front enhances the connection to nature.
Dome in Bennington
4.93 out of 5 average rating, 117 reviews

5BR Rustic Mountain Sanctuary Dome Home

Find connection in this secluded mountainous retreat. Enmeshed in the natural landscape, this space is only accessible via unpaved roads. Even the journey here is part of the adventure. *4WD & Snowtires are needed during winter & early spring due to the possibility of snow or mud* This property requires a lot of upkeep and the steward will likely be onsite during your stay, however the whole house will be exclusively reserved for your booking. This space will rejuvenate & inspire

Top guest favourite
A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.
Home in Bennington
5 out of 5 average rating, 111 reviews

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.

Guest favourite
The kitchen features a blend of modern cabinetry and original brick walls, showcasing a clean, functional design. Open shelving displays glassware and plants. A window allows natural light to fill the space, and a patterned rug adds comfort underfoot.
Flat in Troy
4.96 out of 5 average rating, 208 reviews

Luxury downtown penthouse, near Franklin Plaza.

This beautiful, historic Victorian building is on a short walking distance from Franklin Plaza, one of Troy's most popular wedding and events venues. Just remodeled with a balance of classic and modern design, including original brick in the kitchen and large windows throughout, giving this space beautiful natural light and views. We have security cameras in the first , second floor hallway, outside the front door and back door.There is no cameras inside of the listed units.

Top guest favourite
Flat in Waterford
4.91 out of 5 average rating, 336 reviews

HOT TUB & New Stylish Saratoga County Efficiency

About the space Brand New Everything. This newly created space offers city style interior decor with outside space to enjoy. This includes the New Trex deck with HOT TUB and outdoor relaxation. Situated on large lot- this space offers convenient access to local highways (5 min from I-87, 10 min from 787). Off street parking for 2 vehicles. RV, boat, trailer space available on site. Within 2 min -be at convenience store, pizza shop, ice cream, mini golf, town park and more..

Guest favourite
A rustic cabin constructed with wooden planks and stone features is nestled among tall trees. Lush greenery surrounds the cabin, while a stack of logs is positioned in the foreground. A gravel pathway leads up to the entrance, enhancing the natural setting.
Cabin in West Sand Lake
4.96 out of 5 average rating, 348 reviews

The Lodge at June Farms

See more of us on Prime Video's tv show, June Farms... streaming now! This cabin is a stunning, rustic, open-floor-plan retreat. The screened-in front porch looks down onto our horse pasture. This cabin is our most romantic cabin on the property. Our gigantic rain shower in the bathroom has an 8'x5' wall mirror and a French door that opens out to the forest. If you are a cook, this cabin is a chef's dream. You might also like our stunning new cabin called The Farmhouse.

Top guest favourite
A spacious canvas tent is shown, featuring a queen-sized mattress with natural linens. Two rustic wooden chairs are positioned outside on the wooden deck, with a small table nearby. Natural light enters through the tent's entrance, illuminating the cozy interior.
Farm stay in Johnsonville
4.98 out of 5 average rating, 346 reviews

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.

Guest favourite
An aerial view showcases a charming dark gray townhome surrounded by lush greenery, with the shimmering waters of Saratoga Lake visible in the background. The property features a well-maintained lawn, driveway, and proximity to the lakeshore.
Townhouse in Saratoga Springs
4.83 out of 5 average rating, 114 reviews

Saratoga Lake Front #2; minutes to The Track!

Delightful 3,000 sqft lakefront town home only 15 minutes to the historic Saratoga Springs Track and cultural center, on the east shore of the lake, 3 miles to Brown's Beach. Beautiful and spacious rooms with custom finishes. Cozy fireplace to conquer the cold weather! An amazing place to enjoy the gorgeous sunsets from the private wrap around porch! NEW: 12' Shuffleboard table in the lower level for hours of fun! Also, snowshoes for your use!

Popular amenities for Pittstown holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Rensselaer County
  5. Pittstown