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

Holiday Homes in Whitingham

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is AU$753
includes taxes & fees
8 Sept - 9 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Dining

2. 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 AU$780
includes taxes & fees
15 Sept - 16 Sept
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
In-room safe, iron/ironing board, WiFi, bed sheets

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AU$1,002
includes taxes & fees
9 Sept - 10 Sept
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Property grounds

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

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is AU$470
includes taxes & fees
14 Sept - 15 Sept
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Property grounds

5. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AU$1,293
includes taxes & fees
9 Sept - 10 Sept
Riverbend Berkshire East Basecamp - 3 bedrooms available
Exterior

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

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
The price is AU$954
includes taxes & fees
4 Sept - 5 Sept
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Interior

7. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (64 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 AU$285
includes taxes & fees
7 Sept - 8 Sept
Lovely 2nd Floor Apartment
Exterior

8. 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 AU$458
includes taxes & fees
21 Sept - 22 Sept
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Exterior

9. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AU$304
includes taxes & fees
8 Sept - 9 Sept
Private bed with En-suite bathroom Marigold Room
Iron/ironing board, WiFi, bed sheets

10. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is AU$505
includes taxes & fees
7 Sept - 8 Sept
Cozy private 2 bed apartment in Shelburne Falls
Exterior

11. The Greylock Cabin

The 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 AU$685
includes taxes & fees
14 Sept - 15 Sept
The Greylock Cabin
Dining

12. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (7 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 AU$272
includes taxes & fees
13 Sept - 14 Sept
Cozy Home in Pownal VT
Exterior

13. 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
The price is AU$561
includes taxes & fees
21 Sept - 22 Sept
Two Brooks Lodge
Interior

14. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
The price is AU$376
includes taxes & fees
15 Sept - 16 Sept
Peaceful getaway at birds of a feather
Dining

15. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is AU$657
includes taxes & fees
9 Sept - 10 Sept
A roomy remodeled retreat close to MassMoCA
Property grounds

16. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is AU$865
includes taxes & fees
16 Sept - 17 Sept
Summer Escape Near Lakes, Trails & Mt Snow
Terrace/patio

17. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

Spacious Vermont Farmhouse | 3 Mi to Mount Snow
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is AU$1,142
includes taxes & fees
1 Oct - 2 Oct
Spacious Vermont Farmhouse | 3 Mi to Mount Snow
Coffee/tea maker, fridge, microwave, oven

18. 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 AU$1,572
includes taxes & fees
4 Sept - 5 Sept
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dining

19. 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 AU$808
includes taxes & fees
30 Sept - 1 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Exterior

20. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$607
includes taxes & fees
17 Sept - 18 Sept
North Getaway Cottage
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.
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Top Whitingham Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Hotel was clean and stag was helpful and friendly."
Basil 2-night trip
Posted 17 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Whitingham

Whitingham Holiday Homes information

Number of reviews
295
Accommodation
455 Holiday Homes
Lowest Price
AU$272
Highest Price
AU$1,572