Holiday houses in Greenwich Historic District

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Top-rated holiday rentals in Greenwich Historic District

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Cabin in Shaftsbury
4.99 out of 5 average rating, 484 reviews

Vermont Dream Cabin~70 Acres w/Hot Tub & Fireplace

Log cabin w/ hot tub on 70 acres of Vermont forest with hiking/snowshoe trails, river & mountain stream. Cozy up with wine, games or book by the huge stone woodburning fireplace with fav music from the vintage Bose stereo, enjoy coffee & stargazing on the rocking porch while taking in the mountain views & wildlife or explore the forest & river trails. Enjoy making meals in the ample fully stocked kitchen, the outdoor grill & around the campfire. Crisp AC.*4x4/AWD a MUST for WINTER only BOOKINGS*

Top Guest favourite
Apartment in Greenwich
5 out of 5 average rating, 13 reviews

Cozy Apartment with River Views in Greenwich, NY

Experience the charm of this recently renovated 1800s home, blending historic character with modern amenities. Located on the 1st floor of a multi-family house in the heart of downtown Greenwich, this cozy 2-bedroom apartment offers the perfect escape. Relax on the back patio, overlooking the serene Battenkill River. Nestled in a quiet, friendly neighborhood, the space is within walking distance of local shops, restaurants, and more. Keep it simple at this peaceful and centrally-located place.

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.
Apartment in Greenwich
4.95 out of 5 average rating, 140 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
A charming treehouse is nestled among lush green foliage, featuring a rustic wooden exterior and a wraparound deck. Sunlight filters through the trees, creating a serene atmosphere that invites relaxation and connection with nature.
Treehouse in Argyle
4.99 out of 5 average rating, 128 reviews

Out On a Limb • A Magical Treehouse Experience

Welcome to Out on a Limb, our magical treehouse nestled in the serene woods of upstate New York. This cozy, charming hideaway offers a peaceful & romantic escape, perfect for couples or solo travelers looking to connect with nature. Surrounded by towering trees, the treehouse provides a unique experience year round—from relaxing in the hot-tub on a snowy night, to stargazing by the campfire. The treehouse is always stocked with waffle mix & homemade frozen cookies. We can’t wait to host you!

Superhost
The image features a natural scene with a wooden table in the foreground, adorned with a planter filled with vibrant flowers. Beyond, rolling green fields and distant mountains are visible through a border of trees, showcasing a serene outdoor environment.
Tiny home in Cambridge
4.89 out of 5 average rating, 108 reviews

A Bedroom in the woods with lovely views!

Picturesque location on farmland with views of the mountains. We are a micro farm. Wake up and watch the sunrise and go for a short hike on the property, and get to know the animals. We are located 35 minutes from Saratoga Springs and Lake George, NY and 45 minutes from Dorset and Manchester, VT. Hike the Adirondack or Green Mountains, paddle the streams or go to a nearby small city for a play, a festival, or a concert. There is a long list of things to do and see within an hour of us!

Top Guest favourite
Cabin in Poultney
4.94 out of 5 average rating, 400 reviews

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

Guest favourite
An inviting entrance features a black front door framed by a decorative wreath. A patio area is visible, furnished with a table and chairs, accompanied by a shade umbrella. Gravel pathways and natural stone borders enhance the outdoor space.
Home in Greenwich
4.96 out of 5 average rating, 47 reviews

Farewell Jackson Racing Stables

Relax and unwind with the whole family at the peaceful Farewell Jackson Stables. Located just 15 miles from the Saratoga Race Track, Farewell Jackson is a trying facility for standardbred race horses. The living quarters is a historic barn that has been stylishly remodeled with all the amenities needed to escape the hustle and bustle of life. The name Farewell Jackson is a tribute to our Grandfather, who would dramatically lay down twenty dollar bills while saying Farewell Jackson.

Top Guest favourite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 777 reviews

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.

Top Guest favourite
The cabin's A-frame structure is surrounded by trees, with warm light glowing from the large windows. A spacious deck is visible, featuring outdoor seating. The tranquil landscape offers a serene atmosphere, blending the home harmoniously with nature.
Cabin in Shushan
4.86 out of 5 average rating, 295 reviews

Cozy rustic cabin in the hamlet of Shushan. N.Y.

This cabin overlooks a nature preserve.lots of wildlife,with a peaceful and Serene atmosphere. animals are welcome. the battenkill river is closeby 30 min from Manchester v.t and Saratoga springs ny.cozy up to a fire with a good book,or head out for some designer shopping.hiking trails in Vermont and newyork and plenty of ski resorts ,and snowmobilng.within 30 min. we welcome all animals in the home. enjoy the quiet, and views of shushan NY.here..

Top Guest favourite
Guest suite in Salem
5 out of 5 average rating, 130 reviews

Suite on Salem

Keep it simple at this peaceful and centrally-located place. Walking distance to Salem Central, Fort Salem Theater, the Historic Salem Courthouse, Jacko's, Salem Art Work, On a Limb Bakery, and less than an hour to vermont sking. Come stay in our secure 2-room suite plus bathroom with a separate entrance uniquely filled with local art and antiques. Includes cube-sized refrigerator, coffee maker, and microwave for use.

Guest favourite
A serene view of the Battenkill River is captured in soft fog, with reflections of trees and rocks visible on the water's surface. Gentle ripples create a peaceful ambiance, and lush greenery lines the riverbank, enhancing the tranquil setting.
Campsite in Greenwich
4.92 out of 5 average rating, 134 reviews

"The BattenView" on the Battenkill River

Camp site on the Battenkill River to restore your soul. Enjoy the view, the peace, the river. Kayak, swim, fish, grill, relax next to the firepit, enjoy the wildlife and stargaze. Water & electrical hook-ups provided. Note: RV in photo is no longer available - it is just to show what your experience with your own RV will be like. Two kayaks provided. Total restoration from your hectic daily routine.

Top Guest favourite
A cozy living room features exposed brick walls highlighted by a colorful framed artwork. A white fireplace is centered along the wall, flanked by two framed photographs. Soft lighting comes from sconces, and a wooden coffee table sits between a dark couch and a retro chair.
Apartment in Greenwich
4.92 out of 5 average rating, 53 reviews

Hettie's Place

Located on the second floor of a historic brick building in Greenwich, NY, this fully updated rental blends classic charm with modern comforts. It boasts a spacious large bedroom, bright living room, dedicated workspace, and a stylish retro kitchen. Step onto the small outdoor porch with a BBQ for alfresco dining, and stroll to local shops and eateries to experience the quaint charm of Greenwich.

Popular amenities for Greenwich Historic District holiday rentals