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

Search Vacation Homes in Whitingham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Whitingham vacation 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

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is AED 878
AED 2,061 total
includes taxes & fees
9 Nov - 10 Nov
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is AED 1,201
AED 2,897 total
includes taxes & fees
14 Oct - 15 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

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

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AED 720
AED 2,089 total
includes taxes & fees
26 Oct - 27 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

4. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is AED 1,024
AED 1,685 total
includes taxes & fees
8 Nov - 9 Nov
Greylock Cabin
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

5. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AED 819
AED 2,453 total
includes taxes & fees
9 Nov - 10 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

6. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AED 1,279
AED 2,779 total
includes taxes & fees
13 Oct - 14 Oct
5BR Berkshire Home Mins To The Mountain
A wooden barrel structure with a staircase and railing, surrounded by a forest.

7. Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is AED 1,062
AED 2,512 total
includes taxes & fees
10 Nov - 11 Nov
Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

8. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AED 441
AED 581 total
includes taxes & fees
15 Oct - 16 Oct
The Eagles Wing at The CHM - Private Apartment
A bedroom with a bed, bedside tables, a window, and a radiator.

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

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is AED 659
AED 1,705 total
includes taxes & fees
20 Oct - 21 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

10. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is AED 1,074
AED 2,418 total
includes taxes & fees
13 Oct - 14 Oct
Spacious 5BR w/ Hot Tub & Games
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

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

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is AED 1,702
AED 4,331 total
includes taxes & fees
12 Oct - 13 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A kitchen with white cabinets, a wooden dining table, and pendant lights.

12. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AED 841
AED 1,781 total
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
A two-story house with a porch, surrounded by trees and snow.

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

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 599
AED 1,335 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A hallway with wooden flooring, white walls, and a bed in the background.

14. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is AED 771
AED 1,571 total
includes taxes & fees
12 Oct - 13 Oct
Cozy private 2 bed apartment in Shelburne Falls
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

15. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is AED 511
AED 849 total
includes taxes & fees
1 Nov - 2 Nov
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

16. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 784 total
includes taxes & fees
9 Nov - 10 Nov
Private bed with En-suite bathroom Marigold Room
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

17. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (10 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AED 426
AED 753 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

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

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AED 1,116
AED 2,273 total
includes taxes & fees
13 Oct - 14 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

19. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Stratton
10.0 out of 10, Exceptional, (20 reviews)
"Great spot for a large group. "
United States
Brian G.
The price is AED 1,851
AED 4,179 total
includes taxes & fees
9 Nov - 10 Nov
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

20. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AED 264
AED 382 total
includes taxes & fees
31 Oct - 1 Nov
Cozy Vermont Tiny Home Get Away
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Whitingham Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"Great place to stay....beautiful. Average food"
Gordon 1-night trip
Posted 3 hours ago
The White House Inn

Explore a world of travel with Expedia