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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Whitingham holiday homes

Exterior

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, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is HK$2,015
HK$4,567 total
includes taxes & fees
2 Sept - 3 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Smart TV, fireplace, video games, DVD player

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (61 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
The price is HK$2,812
HK$6,572 total
includes taxes & fees
5 Aug - 6 Aug
Walk To Town, Hottub, Firepit, Games, Mt Snow
Exterior

3. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is HK$2,186
HK$3,630 total
includes taxes & fees
25 Aug - 26 Aug
The Greylock Cabin
Dining

4. 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, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is HK$1,764
HK$4,780 total
includes taxes & fees
26 Aug - 27 Aug
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Property grounds

5. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is HK$1,468
HK$2,672 total
includes taxes & fees
11 Aug - 12 Aug
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Smart TV, fireplace, books

6. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (6 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 HK$2,243
HK$5,317 total
includes taxes & fees
5 Aug - 6 Aug
5BR Berkshire Home Mins To The Mountain
Interior

7. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (60 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is HK$910
HK$1,578 total
includes taxes & fees
9 Aug - 10 Aug
Lovely 2nd Floor Apartment
Property grounds

8. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$1,633
HK$3,698 total
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Smart TV, fireplace, video games, DVD player

9. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (45 reviews)
"Awesome home. Had a great time with the family. Owners were easy to get in touch with."
United States
william k.
The price is HK$2,315
HK$4,867 total
includes taxes & fees
5 Aug - 6 Aug
Summer Escape Near Lakes, Trails & Mt Snow
Terrace/patio

10. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is HK$2,478
HK$5,397 total
includes taxes & fees
5 Aug - 6 Aug
3 Mi to Mount Snow: Spacious West Dover Home
Coffee/tea maker, fridge, microwave, oven

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 HK$3,635
HK$9,247 total
includes taxes & fees
5 Aug - 6 Aug
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Exterior

12. Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 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.
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Coffee/tea maker, fridge, microwave, oven

13. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (52 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is HK$2,579
HK$5,491 total
includes taxes & fees
9 Aug - 10 Aug
Spacious 5BR w/ Hot Tub & Games
Property grounds

14. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
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 HK$2,132
HK$5,212 total
includes taxes & fees
5 Aug - 6 Aug
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Exterior

15. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
Two Brooks Lodge
Living area

16. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is HK$1,465
HK$3,714 total
includes taxes & fees
25 Aug - 26 Aug
Stunning Glass House nestled in the Vermont wilderness!
Dining

17. 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 HK$2,869
HK$5,474 total
includes taxes & fees
16 Aug - 17 Aug
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Iron/ironing board, WiFi, bed sheets

18. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is HK$1,263
HK$2,864 total
includes taxes & fees
9 Aug - 10 Aug
Cozy private 2 bed apartment in Shelburne Falls
Interior

19. Private Cabin 4BR 3BA, Fire pit, Pool table, BBQ Weber, Babbling Brook, Cornhole

Private Cabin 4BR 3BA, Fire pit, Pool table, BBQ Weber, Babbling Brook, Cornhole
Dover
The price is HK$1,137
HK$4,041 total
includes taxes & fees
1 Sept - 2 Sept
Private Cabin 4BR 3BA, Fire pit, Pool table, BBQ Weber, Babbling Brook, Cornhole
Terrace/patio

20. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (37 reviews)
"Great place"
United States
Aidan K.
The price is HK$882
HK$2,086 total
includes taxes & fees
3 Sept - 4 Sept
Peaceful getaway at birds of a feather
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Clean room, quiet, very nice breakfast choices. Did not interact much with staff, just at checkin and checkout. Friendly."
Ray 1-night trip
Posted less than an hour ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Whitingham

Whitingham Vacation Homes information

Number of reviews
378
Accommodation
459 Vacation Homes
Lowest Price
HK$1,578
Highest Price
HK$9,247

Explore a world of travel with Expedia