Whitingham Vacation Homes

A rural landscape with rolling hills, a winding road, and autumn-colored trees.

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Our top choices for Whitingham holiday homes

A cozy living room with a beige sofa, a wooden coffee table, and two lamps.

1. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Whitingham

Jonathan

HK$3,997 total

includes taxes & fees

27 Oct - 28 Oct

A cozy interior with a wooden ceiling, a large window, and a table with chairs.

2. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington

Natalie

HK$4,487 total

includes taxes & fees

26 Oct - 27 Oct

A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

3. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

Dana W.

HK$3,054 total

includes taxes & fees

9 Nov - 10 Nov

A snow-covered wooden cabin with a balcony, surrounded by snow-covered trees.

4. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

Wilmington

HK$5,046 total

includes taxes & fees

27 Oct - 28 Oct

A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

5. The Eagles Wing at The CHM - Private Apartment

Dover

Ava M.

HK$1,542 total

includes taxes & fees

26 Oct - 27 Oct

A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

6. Walk To Town, Hottub, Firepit, Games, Mt Snow

Wilmington

Jeremy P.

HK$6,053 total

includes taxes & fees

27 Oct - 28 Oct

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

7. Greylock Cabin

Florida

Margaret M.

HK$3,606 total

includes taxes & fees

22 Nov - 23 Nov

A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

8. Modern Mount Snow Gnarvana - Steps to Carinthia

Dover

Lynn B.

HK$3,257 total

includes taxes & fees

26 Oct - 27 Oct

A two-story house with a porch, surrounded by trees and snow.

9. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

10. Private room with En-suite bathroom Marigold Room

Shelburne Falls

HK$1,621 total

includes taxes & fees

26 Oct - 27 Oct

A modern interior with large windows, a wooden ceiling, and a cozy seating area.

11. Stunning Glass House nestled in the Vermont wilderness!

Guilford

Chris O.

HK$3,974 total

includes taxes & fees

8 Nov - 9 Nov

A kitchen with white cabinets, a wooden dining table, and pendant lights.

12. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

HK$3,776 total

includes taxes & fees

30 Oct - 31 Oct

A narrow hallway with a wooden ceiling, white walls, a staircase, and a bookshelf with books.

13. Cozy Vermont Tiny Home Get Away

Brattleboro

HK$815 total

includes taxes & fees

4 Nov - 5 Nov

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

14. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

A wooden barrel structure with a staircase and railing, surrounded by a forest.

15. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

Dover

Connor S.

HK$5,165 total

includes taxes & fees

1 Nov - 2 Nov

A hallway with wooden flooring, white walls, and a bed in the background.

16. Shelburne Falls on Main

Shelburne Falls

maureen

HK$3,270 total

includes taxes & fees

26 Oct - 27 Oct

A spacious kitchen with wooden flooring, a central island with stools, a dining table, and pendant lighting.

17. Spacious 5BR w/ Hot Tub & Games

Colrain

Griffin S.

HK$5,128 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living room with a fireplace, a dining area, and a kitchen with wooden cabinets and a microwave.

18. Experience Vermont’s Fall Magic at here at the Lemondrop

Dover

Alexander H.

HK$5,167 total

includes taxes & fees

31 Oct - 1 Nov

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

19. Cozy Home in Pownal VT

Pownal

Jeri R.

HK$1,608 total

includes taxes & fees

26 Oct - 27 Oct

A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

20. Lovely 2nd Floor Apartment

Greenfield

Jane P.

HK$1,953 total

includes taxes & fees

27 Oct - 28 Oct

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Top Whitingham Hotel Reviews

The White House Inn

10/10 Excellent

"Very welcoming gracious staff in a beautiful and charming facility, on a beautiful site and grounds, with a very comfortable and spacious room. We will be returning in future years to this very special place. Many thanks to entire staff and management. Bill & Heather C."

Latchis Hotel

8/10 Good

"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."

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