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

Whitingham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Whitingham vacation 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 CA $279
CA $710 total
includes taxes & fees
Oct 29 - Oct 30
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 CA $274
CA $798 total
includes taxes & fees
Oct 29 - Oct 30
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

3. 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 CA $174
CA $550 total
includes taxes & fees
Oct 27 - Oct 28
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A snow-covered wooden cabin with a balcony, surrounded by snow-covered trees.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is CA $290
CA $907 total
includes taxes & fees
Nov 1 - Nov 2
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

5. 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 CA $216
CA $275 total
includes taxes & fees
Oct 29 - Oct 30
The Eagles Wing at The CHM - Private Apartment
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

6. 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 CA $431
CA $1,081 total
includes taxes & fees
Oct 25 - Oct 26
Walk To Town, Hottub, Firepit, Games, Mt Snow
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

7. 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 CA $390
CA $641 total
includes taxes & fees
Nov 22 - Nov 23
Greylock Cabin
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 CA $175
CA $581 total
includes taxes & fees
Oct 26 - Oct 27
Modern Mount Snow Gnarvana - Steps to Carinthia
A two-story house with a porch, surrounded by trees and snow.

9. 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.
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.

10. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $161
CA $289 total
includes taxes & fees
Oct 27 - Oct 28
Private room with En-suite bathroom Marigold Room
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

11. 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 CA $289
CA $703 total
includes taxes & fees
Nov 8 - Nov 9
Stunning Glass House nestled in the Vermont wilderness!
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 CA $321
CA $679 total
includes taxes & fees
Oct 30 - Oct 31
A roomy remodeled retreat close to MassMoCA
A narrow hallway with a wooden ceiling, white walls, a staircase, and a bookshelf with books.

13. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is CA $101
CA $146 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Vermont Tiny Home Get Away
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

14. 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 CA $455
CA $1,028 total
includes taxes & fees
Oct 25 - Oct 26
5BR Berkshire Home Mins To The Mountain
A wooden barrel structure with a staircase and railing, surrounded by a forest.

15. Dover Mountain Retreat with Hot Tub Near Mt. Snow

Dover Mountain Retreat with Hot Tub Near Mt. Snow
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 CA $367
CA $914 total
includes taxes & fees
Nov 1 - Nov 2
Dover Mountain Retreat with Hot Tub Near Mt. Snow
A hallway with wooden flooring, white walls, and a bed in the background.

16. Shelburne Falls on Main

Shelburne Falls on Main
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 CA $282
CA $584 total
includes taxes & fees
Oct 27 - Oct 28
Shelburne Falls on Main
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

17. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (56 reviews)
"This home was comfy, really clean and hosts were easy to reach and chat with during our stay. My extended family had a great time getting together this summer staying at hosts’ home!"
United States
Griffin S.
The price is CA $409
CA $925 total
includes taxes & fees
Oct 27 - Oct 28
Spacious 5BR w/ Hot Tub & Games
A pathway through a forest with autumn leaves and a wooden bridge.

18. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is CA $475
CA $949 total
includes taxes & fees
Oct 25 - Oct 26
Experience Vermont’s Fall Magic at here at the Lemondrop
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

19. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (12 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 CA $163
CA $287 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Home in Pownal VT
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

20. 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 CA $214
CA $352 total
includes taxes & fees
Nov 3 - Nov 4
Lovely 2nd Floor Apartment
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

The Williams Inn

The Williams Inn

10/10 Excellent
"The staff and ambience are wonderful!"
Silvia 1-night trip
Posted 1 hour ago
The Williams Inn

Find out more about Whitingham

Whitingham Vacation Homes information

Number of reviews
444
Accommodation
445 Vacation Homes
Lowest Price
CA $146
Highest Price
CA $1,081

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