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

Our top choices for Whitingham vacation rentals

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
$457 nightly
The price is $512
Nov 2 - Nov 3
Total with taxes and fees
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

2. 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 22 - Oct 23
Total with taxes and fees
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
A two-story blue house with a porch, surrounded by a garden with orange flowers.

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

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (36 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
$132 nightly
The price is $148
Oct 18 - Oct 19
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

4. 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.
$273 nightly
The price is $309
Oct 19 - Oct 20
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A wooden interior with a kitchen, bar area, and dining space.

5. 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, (7 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.
$232 nightly
The price is $260
Nov 2 - Nov 3
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A calm lake with a wooden boat on the shore.

6. 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.
$271 nightly
The price is $306
Nov 1 - Nov 2
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

7. 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.
$168 nightly
The price is $190
Oct 23 - Oct 24
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A window with a view of a forested landscape and a wooden deck.

8. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
$435 nightly
The price is $487
Nov 2 - Nov 3
Total with taxes and fees
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A bedroom with a bed, bedside tables, a window, and a radiator.

9. 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.
$363 nightly
The price is $410
Oct 19 - Oct 20
Total with taxes and fees
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

10. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
$319 nightly
The price is $361
Oct 18 - Oct 19
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

11. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
$167 nightly
The price is $187
Oct 18 - Oct 19
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

12. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$402 nightly
The price is $454
Oct 18 - Oct 19
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

13. 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 19 - Oct 20
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

14. 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
8.8 out of 10, Excellent, (6 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 19 - Oct 20
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
$621 nightly
The price is $648
Oct 20 - Oct 21
Total with taxes and fees
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A wooden house with a porch lit by string lights, surrounded by snow.

16. 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.
$407 nightly
The price is $460
Nov 4 - Nov 5
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

17. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$165 nightly
The price is $184
Nov 4 - Nov 5
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

18. 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.
$683 nightly
The price is $772
Oct 19 - Oct 20
Total with taxes and fees
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.

19. 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.
$379 nightly
The price is $429
Oct 18 - Oct 19
Total with taxes and fees
Modern Mount Snow Gnarvana - Steps to Carinthia
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

20. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$191 nightly
The price is $213
Nov 16 - Nov 17
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
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 Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"We had a wonderful time in Bennington. Breakfast at the hotel was typical hotel continental but we found more interesting places at which to indulge. Rooms were clean. Not sound proof but not too noisy once we were ready to sleep. Also there is no elevator so be prepared to carry luggage! Overall I would still stay again because the town is lovely!!"
Malinda 2-night trip
Posted 3 hours ago
Hotel Vervana, Trademark Collection by Wyndham

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 $260 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.