Westmoreland Vacation Rentals from $158: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Westmoreland has to offer?

Family Friendly Hilltop House In Putney Vermont : Visitors like this Westmoreland vacation home rental. It is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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Our top choices for Westmoreland vacation rentals

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Hinsdale

Gina M.

$171 nightly

Jul 13 - Jul 14

Total with taxes and fees

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

$326 nightly

Jul 9 - Jul 10

Total with taxes and fees

2 private mountain RV pads for rent. Full hook ups

Winchester

$75 nightly

Jul 9 - Jul 10

Total with taxes and fees

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Roy-michael G.

$356 nightly

Jul 9 - Jul 10

Total with taxes and fees

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

Dover

Tania J.

$286 nightly

Jul 9 - Jul 10

Total with taxes and fees

The MountainTop - Stratton & Mt Snow - Fire Pit

Stratton

Brenna G.

$355 nightly

Jul 9 - Jul 10

Total with taxes and fees

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Wardsboro

Jeff H.

$383 nightly

Aug 4 - Aug 5

Total with taxes and fees

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

Brattleboro

James M.

$275 nightly

Jul 9 - Jul 10

Total with taxes and fees

Smart TV, fireplace, Netflix, streaming services

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

Dover

Brian S.

$413 nightly

Jul 13 - Jul 14

Total with taxes and fees

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

Dover

Evan C.

$320 nightly

Jul 9 - Jul 10

Total with taxes and fees

John's Mountain Hideaway

Jaffrey

Lori S.

$486 nightly

Jul 15 - Jul 16

Total with taxes and fees

Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Susan S.

$251 nightly

Jul 21 - Jul 22

Total with taxes and fees

Stunning Glass House nestled in the Vermont wilderness!

Guilford

"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."

Grant D.

$444 nightly

Jul 22 - Jul 23

Total with taxes and fees

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Wardsboro

Carly L.

$486 nightly

Jul 13 - Jul 14

Total with taxes and fees

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Townshend

David D.

$346 nightly

Jul 12 - Jul 13

Total with taxes and fees

Family Friendly Hilltop House In Putney Vermont

Putney

Susan O.

$294 nightly

Jul 13 - Jul 14

Total with taxes and fees

Vikings Villages Resort - Double Bed Room

Guilford

$336 nightly

Jul 12 - Jul 13

Total with taxes and fees

Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Stephanie F.

$376 nightly

Jul 30 - Jul 31

Total with taxes and fees

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

West Dover

Dan G.

$590 nightly

Jul 9 - Jul 10

Total with taxes and fees

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole

Frances D.

$266 nightly

Jul 9 - Jul 10

Total with taxes and fees

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Top Westmoreland Hotel Reviews

Days Inn by Wyndham Keene NH

8/10 Good

"Pros: + Air conditioned + Free parking + Free breakfast + Free wifi + Nice people + Cheapest hotel in Keene Cons: - Half of the outlets in the room didn't work - No pool Overall a good deal."

Vikings Villages Resort

10/10 Excellent

"We had an amazing stay at Viking Village resort! It is an absolute hidden gem and truly felt like a fairytale escape. The cozy wooden houses are free-standing, which gives you excellent privacy, making them perfect for either a family trip or a solo getaway. I was so pleasantly surprised to find a fully equipped kitchen inside. The entire area is incredibly quiet with absolutely no outside noise—just total peace. On the premises, they have a great fireplace setup and the most amazing, cute goats! My only regret is that we only stayed for one night. We are already hoping to come back for a longer stay next time. It is absolutely worth the drive!"

Comfort Inn & Suites Brattleboro I-91

8/10 Good

"The location is very convenient, right off I-91. Overall, we had a good experience. However, when we first entered the room, it was freezing because the A/C was set to 54°F. During the night, the unit started making loud, erratic noises, so I turned it off, but the noise continued. It kept disturbing us until we finally fell asleep late at night. I even removed the batteries from the thermostat, but the noise still didn’t stop."

Latchis Hotel

10/10 Excellent

"I love this place. It's really special. Some people to preserve what was special and exciting and authentic about a historic space and these are my people. They have the amenities you need (great bed and linens, refridgerator, microwave, good towels). They have the amenities you don't need but love! (record players in all rooms and throughout the hotel and vintage vinyl readily available, cucumber water in the lobby, a coffe and tea station in the lobby, a postcard writing station, easy access to a movie theater). This won't be everybodies cup of tea. What used to be luxury amenities are preserved a curiousities, the halls feel like a dorm, and brattleboro is on a downturn. But Brattleboro is also really beauitful, with some lovely restaurants and arts venues. And I love everything about it. If you stay - make sure to stay see a movie. It's gorgeous in there. Turkish breakfast at Tulip in amazing. Shim La's really good. check out the river. Stone Church is a fun venue. And Ther'es a lot to see and love in brattleboro. Also Go to chesterfield and check out madame sherri's castle and the gorge. Enjoy!"

Find out more about Westmoreland

Everything you need to know about Westmoreland 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 Westmoreland 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 Westmoreland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westmoreland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westmoreland. 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 Westmoreland 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 $158 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 Westmoreland rentals

At Expedia, we put the best Westmoreland 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 Westmoreland 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 Westmoreland 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 Westmoreland. 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 a vacation rental in Westmoreland?

Yes, we give you a choice of vacation rentals close to popular points of interest in Westmoreland, or you can go with a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Westmoreland has to offer?

Family Friendly Hilltop House In Putney Vermont: Visitors like this Westmoreland vacation home rental. It is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Westmoreland?

Explore the area and family-friendly sights such as Cheshire Children's Museum, or get out into nature at a spot like Connecticut River. Spofford Lake and Landmark College are a couple of places you'll find in the larger area.

What’s a vacation rental in Westmoreland like?

Vacation rentals are private properties you can book for short or long periods in Westmoreland. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for small groups.

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Check prices for these dates

Our top choices for Westmoreland vacation rentals

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2 private mountain RV pads for rent. Full hook ups

Chalet Mount Snow/Stratton Skiing/hiking

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

The MountainTop - Stratton & Mt Snow - Fire Pit

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

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

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

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

John's Mountain Hideaway

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Stunning Glass House nestled in the Vermont wilderness!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Family Friendly Hilltop House In Putney Vermont

Vikings Villages Resort - Double Bed Room

Charming Chester Farmhouse near Near VT Slopes

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Find vacation rentals that suit your style

Top Westmoreland Hotel Reviews

Days Inn by Wyndham Keene NH

Windmill Motel Restaurant

Best Western Plus Keene Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Vikings Villages Resort

Colonial Motel

Comfort Inn & Suites Brattleboro I-91

Courtyard by Marriott Keene Downtown

Latchis Hotel

Find out more about Westmoreland

Frequently asked questions

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