Top Vacation Homes in Sullivan County in 2026

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Top cities in Sullivan County

A town with historic buildings, a church, and mountains in the background.

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Our top choices for Sullivan County vacation homes

A snow-covered building with a clock tower, surrounded by other buildings with balconies.

1. Okemo Mountain Lodging by Vail Resorts

Clock Tower Base Area

"The unit was very clean. However, there was a distinct musty/moldy smell throughout the unit as if had been sitting for quite sometime. We did bring a scented candle to help and was able to use the fireplace which also helped with the smell. All and all, for an older unit, the stay was not bad, the neighbors were great and it was peaceful aling with a beautiful view. We would like to stay there again."

Patricia

2. The Inn at Kampfires

Brattleboro

Nancy E

A child sliding down a water slide shaped like a frog, with a pool area in the background.

3. Mountain Lodge At Okemo-1br Fireplace & Updated Kitchen 1 Bedroom Condo by RedAwning

Clock Tower Base Area

A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

4. Brook Road Condo

Goshen

Margaret

NT$9,843 total

includes taxes & fees

Nov 16 - Nov 17

A cozy cabin interior with a fireplace, wooden furniture, and large windows.

5. The Grafton Lodge Secluded Green Mountain Escape

Grafton

6. Cobb Hill Estate

Harrisville

A modern kitchen with a large island, wooden ceiling, and white cabinetry.

7. Treehouse Home

Ludlow

A wooden deck with a railing overlooking a body of water, surrounded by trees.

8. Temple's Sunset Harbor

Newbury

A cozy living room with leather sofas, a fireplace, and a chessboard.

9. Luxury 6br Solitude Ge- Indoor Bball Court, Private Tub 6 Bedroom Home by RedAwning

Ludlow

10. Immaculate - Stratton, Mount Snow

East Jamaica

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Top reviews in Sullivan County

A bar area with a cake on a glass stand, plates, a pink napkin, and a rolled dessert on a plate.

Rosewood Country Inn

Bradford

10/10 Excellent

Anonymous traveler

A large white house with a well-maintained lawn and outdoor seating area.

The Lyme Inn

Lyme

10/10 Excellent

gayle

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A large estate with multiple buildings, a swimming pool, and a well-maintained lawn.

Blue Bear Inn

Francestown

10/10 Excellent

Margaret

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

A wooden dock leading to a stone staircase with a view of a white house and green chairs by a lake.

Follansbee Inn

North Sutton

10/10 Excellent

The owners are so kind, friendly, and thoughtful! I stayed here the night before the eclipse, and because they knew people wanted to leave early the next day to beat the eclipse traffic, they moved up the start of breakfast (poached eggs and bacon hash, yum!) an hour. The hotel is beautiful and has wonderful views of the surroundings, including the lake, from windows. There is a nice loop around the lake that can be done, and hiking trails nearby. There is a cozy atmosphere in the winter,...

Christina

A wooden cabinet with glass doors, a mirror, and a vase with flowers.

Colby Hill Inn

Henniker

10/10 Excellent

Mary Clancy

A dock extending into a lake with a grassy area in the foreground and trees in the background.

Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

10/10 Excellent

James

A modern outdoor lounge area with two lounge chairs and a wooden deck.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Anonymous traveler

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John