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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Whitingham vacation rentals

A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

1. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (9 reviews)
"A beautiful, clean, and cozy stay. The modern space was bright and well-equipped with everything we needed, and the hot tub made it especially relaxing."
United States
Nicole H.
$705 nightly
The price is $790
Oct 14 - Oct 15
Total with taxes and fees
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
An aerial view of a house surrounded by a forest with autumn foliage.

2. 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
$503 nightly
The price is $563
Oct 28 - Oct 29
Total with taxes and fees
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

3. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.4 out of 10, Very good, (5 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
$576 nightly
The price is $645
Oct 5 - Oct 6
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

4. 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.
$734 nightly
The price is $829
Oct 4 - Oct 5
Total with taxes and fees
Walk To Town, Hottub, Firepit, Games, Mt Snow
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

5. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
$366 nightly
The price is $403
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

6. 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
$538 nightly
The price is $572
Oct 6 - Oct 7
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

7. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Once we got to know the fireplace, it was a wonderful addition to a very cozy cabin. The house felt loved and each different room had different touches of character and magic. We absolutely loved our stay. "
United States
Sarah K.
$375 nightly
The price is $424
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

8. 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.
$679 nightly
The price is $767
Oct 9 - Oct 10
Total with taxes and fees
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
A wooden interior with a kitchen, bar area, and dining space.

9. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (5 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$236 nightly
The price is $264
Oct 5 - Oct 6
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

10. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
$279 nightly
The price is $315
Oct 26 - Oct 27
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A log cabin with a balcony, surrounded by trees.

11. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (54 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
$536 nightly
The price is $599
Oct 5 - Oct 6
Total with taxes and fees
Bear Creek Cabin
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

12. 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.
$654 nightly
The price is $730
Oct 4 - Oct 5
Total with taxes and fees
5BR Berkshire Home Mins To The Mountain
A two-story blue house with a porch, surrounded by a garden with orange flowers.

13. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
$141 nightly
The price is $158
Oct 4 - Oct 5
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

14. 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.
$424 nightly
The price is $459
Oct 29 - Oct 30
Total with taxes and fees
The Greylock Cabin
A wooden house with a porch lit by string lights, surrounded by snow.

15. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$357 nightly
The price is $403
Oct 1 - Oct 2
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

16. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
$1,165 nightly
The price is $1,301
Oct 20 - Oct 21
Total with taxes and fees
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A dining area with a long table and chairs, large windows with a view of trees, and a barbecue grill outside.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
$653 nightly
The price is $683
Oct 6 - Oct 7
Total with taxes and fees
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A calm lake with a wooden boat on the shore.

18. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
$262 nightly
The price is $296
Oct 13 - Oct 14
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A two-story white house with a red door, surrounded by autumn foliage and a stone wall.

19. 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.
$129 nightly
The price is $146
Oct 6 - Oct 7
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

20. 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.
$640 nightly
The price is $715
Oct 4 - Oct 5
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
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

Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"The staff was very helpful and the breakfasts were great! Lots of healthy options and plenty of excellent fresh fruit and some for the road, too. We'll be back."
William 2-night trip
Posted 2 hours ago
Willows Motel Williamstown

Find out more about Whitingham

Everything you need to know about Whitingham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Whitingham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Whitingham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Whitingham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Whitingham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Whitingham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $337 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Whitingham rentals

At Expedia, we put the best Whitingham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Whitingham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Whitingham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Whitingham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Whitingham?

Yes, we offer vacation rentals near popular local attractions in Whitingham, or you can select a more secluded option if you'd like a relaxing place to stay. Whitingham is known for its wineries and parks.

What's the top vacation rental in Whitingham?

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating : Visitors give good reviews to this Whitingham vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Another good choice for your trip to Whitingham is Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing.

How many vacation rentals are there in Whitingham?

Expedia has 14 vacation rentals for your stay in Whitingham.

What’s there to see and do in Whitingham?

Harriman Reservoir and Deerfield River are a couple of lovely local spots to get outside and enjoy nature. Green Mountain National Forest and Jacksonville Pond are a couple of places you'll find in the larger area.

What are vacation rentals like in Whitingham?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Whitingham. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family gatherings.