Holiday rentals 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
Flat 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.

Top guest favourite
A charming home is nestled among trees on a peaceful lakefront. A large deck with a red umbrella overlooks the water, while a private dock extends into the lake. Various outdoor activities and relaxation areas are visible, enhancing the serene setting.
Home in Argyle
5 out of 5 average rating, 47 reviews

Lakefront gem

A great location on a peaceful lake. Located on a private peninsula, this lovely home includes a 12x12 floating dock, a boat dock, kayaks, canoe, and stand-up paddle board for use. Fishing poles are also available for use in this great fishing spot! There is a hammock, a Weber grill, and plenty of Adirondack chairs to relax around the gas and/or wood fire pit (firewood available) on the large stone patio. Inside includes an open floorplan, a stone fireplace, and a sunroom overlooking the lake.

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
4.96 out of 5 average rating, 136 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, 121 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!

Top guest favourite
Cabin in Shaftsbury
4.99 out of 5 average rating, 326 reviews

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!

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
4.88 out of 5 average rating, 103 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!

Superhost
Treehouse in Jamaica
5 out of 5 average rating, 3 reviews

The Treehouse at Frog Pond Farm

The treehouse is anything but ordinary, with mountain views from the bedroom loft, a walkway in the trees to a screened in porch, a slate tile shower with a window, a cozy reading nook to relax in while watching the snow pile up on the evergreen trees, a warming gas stove to enjoy the ambiance, and a comfy organic bed, sheets and towels to rejuvenate. You can walk down to the pond to enjoy the frogs and peepers or to the chicken coop for some fresh eggs in the morning.

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, 772 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, 292 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..

Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham
4.9 out of 5 average rating, 110 reviews

The House of Pi

Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

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, 131 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.
Flat in Greenwich
4.94 out of 5 average rating, 51 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