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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Whitingham vacation rentals

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, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
$514 nightly
The price is $576
Sep 2 - Sep 3
Total with taxes and fees
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Coffee/tea maker, fridge, microwave, stovetop

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, (7 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
Aug 19 - Aug 20
Total with taxes and fees
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Exterior

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

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (33 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
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Private kitchen

4. 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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
$230 nightly
The price is $258
Aug 9 - Aug 10
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Outdoor pool, a heated pool

5. 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.
$289 nightly
The price is $327
Aug 10 - Aug 11
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Terrace/patio

6. 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)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
$405 nightly
The price is $458
Aug 11 - Aug 12
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Beach

7. 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)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
$256 nightly
The price is $290
Aug 20 - Aug 21
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
House (3 Bedrooms) | Front of property

8. 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
$395 nightly
The price is $435
Aug 11 - Aug 12
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Living area

9. 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
9.0 out of 10, Wonderful, (4 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.
$535 nightly
The price is $599
Aug 11 - Aug 12
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Lobby

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.
$320 nightly
The price is $362
Aug 10 - Aug 11
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Exterior

11. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$389 nightly
The price is $439
Aug 13 - Aug 14
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Smart TV, fireplace, Netflix, streaming services

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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$420 nightly
The price is $475
Sep 1 - Sep 2
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Interior

13. 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
10.0 out of 10, Exceptional, (1 review)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
$178 nightly
The price is $199
Aug 10 - Aug 11
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Dining

14. 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.
$593 nightly
The price is $634
Aug 26 - Aug 27
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Property grounds

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

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
$301 nightly
The price is $337
Aug 17 - Aug 18
Total with taxes and fees
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Exterior

16. Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
$364 nightly
The price is $408
Aug 31 - Sep 1
Total with taxes and fees
Perfect for a peaceful get away in clean fresh Vermont air!
1 bedroom, desk, iron/ironing board, WiFi

17. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
$191 nightly
The price is $214
Aug 30 - Aug 31
Total with taxes and fees
Balcony Room in Victorian Home private bath
Outdoor dining

18. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$257 nightly
The price is $289
Aug 23 - Aug 24
Total with taxes and fees
New Studio In Town, By the Water
Smart TV, fireplace, video games, DVD player

19. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (61 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
$736 nightly
The price is $831
Aug 10 - Aug 11
Total with taxes and fees
Walk To Town, Hottub, Firepit, Games, Mt Snow
Interior

20. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (60 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.
$180 nightly
The price is $201
Aug 9 - Aug 10
Total with taxes and fees
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

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"Visiting family in Greenfield and really only needed a spot with a clean bed. I was pleasantly surprised by the Hampton Inn. Room was clean and staff was friendly and helpful. We didn't eat breakfast there, but did enjoy the free coffee in the lobby. Only odd thing about this hotel is its location. The entrance to the hotel is from the back of the parking lot of the 99 restaurant. Next time I visit, I'm staying here."
Shirin 2-night trip
Posted 3 hours ago
Hampton Inn & Suites Greenfield

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 $157 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?

Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing: Visitors give good reviews to this Whitingham vacation home rental, which is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a hot tub. Another good choice for your trip to Whitingham is Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating .

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.