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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Whitingham holiday homes

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

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

Mt Snow Ski Escape • Fire Pit • Arcade • 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 HK$1,585
HK$4,017 total
includes taxes & fees
2 Nov - 3 Nov
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
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!

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 HK$1,570
HK$4,499 total
includes taxes & fees
18 Nov - 19 Nov
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is HK$1,162
HK$1,490 total
includes taxes & fees
23 Oct - 24 Oct
The Eagles Wing at The CHM - Private Apartment
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is HK$1,625
HK$5,085 total
includes taxes & fees
20 Oct - 21 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is HK$1,093
HK$3,219 total
includes taxes & fees
19 Oct - 20 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

6. 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 HK$2,040
HK$3,410 total
includes taxes & fees
12 Nov - 13 Nov
Greylock Cabin
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

7. 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 HK$2,417
HK$6,057 total
includes taxes & fees
19 Oct - 20 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
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

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is HK$1,017
HK$3,322 total
includes taxes & fees
19 Oct - 20 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

9. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 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$1,746
HK$4,127 total
includes taxes & fees
18 Nov - 19 Nov
Stunning Glass House nestled in the Vermont wilderness!
A two-story house with a porch, surrounded by trees and snow.

10. 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 HK$1,193
HK$2,738 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

11. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is HK$942
HK$1,674 total
includes taxes & fees
16 Nov - 17 Nov
Private bed with En-suite bathroom Marigold Room
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

12. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is HK$565
HK$816 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Vermont Tiny Home Get Away
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

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 HK$2,549
HK$5,740 total
includes taxes & fees
19 Oct - 20 Oct
5BR Berkshire Home Mins To The Mountain
A wooden barrel structure with a staircase and railing, surrounded by a forest.

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$2,226
HK$5,316 total
includes taxes & fees
10 Nov - 11 Nov
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
A kitchen with white cabinets, a wooden dining table, and pendant lights.

15. 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 HK$1,797
HK$3,805 total
includes taxes & fees
19 Oct - 20 Oct
A roomy remodeled retreat close to MassMoCA
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

16. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 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 HK$1,123
HK$1,851 total
includes taxes & fees
26 Oct - 27 Oct
Lovely 2nd Floor Apartment
A hallway with wooden flooring, white walls, and a bed in the background.

17. 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 HK$1,648
HK$3,358 total
includes taxes & fees
19 Oct - 20 Oct
Cozy private 2 bed apartment in Shelburne Falls
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

18. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (11 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is HK$911
HK$1,609 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Home in Pownal VT
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

19. 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$3,638
HK$9,254 total
includes taxes & fees
19 Oct - 20 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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

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$2,384
HK$4,856 total
includes taxes & fees
19 Oct - 20 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
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
"Would stay here again for sure"
Jennifer 1-night trip
Posted 5 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Whitingham

Whitingham Vacation Homes information

Number of reviews
356
Accommodation
441 Vacation Homes
Lowest Price
HK$816
Highest Price
HK$9,254

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