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

An aerial view of a house surrounded by a forest with autumn foliage.

1. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

Jonathan

HK$4,429 total

includes taxes & fees

28 Oct - 29 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$4,463 total

includes taxes & fees

27 Oct - 28 Oct

A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

3. The Eagles Wing at The CHM - Private Apartment

Dover

Ava M.

HK$1,543 total

includes taxes & fees

13 Oct - 14 Oct

A wooden staircase leading to a cabin with a balcony, surrounded by trees.

4. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

Wilmington

Alex B.

HK$6,012 total

includes taxes & fees

9 Oct - 10 Oct

A bedroom with a bed, bedside tables, a window, and a radiator.

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

Woodford

HK$3,747 total

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

6. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

Wilmington

HK$5,552 total

includes taxes & fees

28 Oct - 29 Oct

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

7. Greylock Cabin

Florida

Margaret M.

HK$3,599 total

includes taxes & fees

29 Oct - 30 Oct

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

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

Wilmington

Jeremy P.

HK$6,358 total

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a skylight, a bed with floral bedding, a bedside table, and a nightstand.

9. Cozy Vermont Tiny Home Get Away

Brattleboro

HK$832 total

includes taxes & fees

30 Oct - 31 Oct

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

10. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

HK$1,683 total

includes taxes & fees

25 Oct - 26 Oct

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

11. Lovely 2nd Floor Apartment

Greenfield

Christa B.

HK$1,823 total

includes taxes & fees

22 Oct - 23 Oct

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.

12. Modern Mount Snow Gnarvana - Steps to Carinthia

Dover

Lynn B.

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

13. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

HK$5,384 total

includes taxes & fees

6 Oct - 7 Oct

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

14. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

HK$3,769 total

includes taxes & fees

14 Oct - 15 Oct

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

15. Cozy Home in Pownal VT

Pownal

Jess M.

HK$1,600 total

includes taxes & fees

8 Oct - 9 Oct

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

16. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

HK$3,357 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

17. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Dover

jim f.

HK$9,252 total

includes taxes & fees

5 Oct - 6 Oct

A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

18. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

West Dover

ken g.

HK$6,649 total

includes taxes & fees

16 Oct - 17 Oct

A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

19. Spacious 5BR w/ Hot Tub & Games

Colrain

Staci M.

HK$5,245 total

includes taxes & fees

4 Oct - 5 Oct

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

20. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

HK$4,855 total

includes taxes & fees

1 Nov - 2 Nov

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Top Whitingham Hotel Reviews

Hampton Inn Brattleboro

10/10 Excellent

"We stay here 2 or 3 times a year and know it well. The staff are always welcoming and helpful. On this visit, we found our original room to be noisy because of the ice machine (?), but the staff got us another room when asked. The room was spacious, quiet and comfortable. The hotel was unusually full, but very quiet. Breakfast is always good here and the coffee is excellent. (Vermont seems to be obsessed with coffee....) Having tried two or three other hotels in Brattleboro, we have settled on the Hampton Inn as our "go to" spot."

The Porches Inn at Mass MoCA

10/10 Excellent

"Excellent staff. Friendly and helpful. Enjoyed the pool and sauna. Breakfast above average. One little quirk with the room. There was a frosted window on the wall of the bathroom so when you turned on the bathroom light it illuminated the bedroom. Could have done without that. But all the rooms are different. Good location across from Mass MoCA. Overall would recommend."

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