Westmoreland Vacation Rentals

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Dec 31 - Jan 1
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Jan 1 - Jan 2
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Jan 9 - Jan 11

Our top choices for Westmoreland vacation rentals

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

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.2 out of 10, Wonderful, (17)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is ￥7,749
￥46,826 total
includes taxes & fees
Jan 5 - Jan 6, 2026
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is ￥21,836
￥47,515 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Lake Whitingham & Mount Snow Area Village Apartment
2 bedrooms, desk, free WiFi
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin in Jamaica

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is ￥18,810
￥35,179 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
Fridge, microwave, oven, stovetop
Lake Front Family Friendly Escape

Vacation Home in Newport

Lake Front Family Friendly Escape
10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is ￥16,845
￥53,816 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lake Front Family Friendly Escape
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is ￥21,056
￥39,829 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Cabin in Fitzwilliam

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is ￥19,512
￥32,847 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (46)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is ￥15,597
￥47,939 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Vacation Home in Stoddard

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
10.0 out of 10, Exceptional, (1)
"Place was clean, cozy & very relaxing.. accommodating & communicative host provided us with necessary info for great week! Beautiful lake & landscape was great viewing during surprise snowstorm! Our Thanksgiving week was wonderful as we enjoyed lovely, quiet area in spacious 4 bdrm/2 bath home! Will definitely consider returning"
United States
Jeannie M.
The price is ￥50,690
￥94,260 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Vacation Home in Keene

Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is ￥19,886
￥43,238 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Downtown Hot Tub Escape
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Chalet in East Dover

Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥19,426
￥68,739 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
Property grounds
The Studio with a View. Bring your dog, too!

Cabin in Brattleboro

The Studio with a View. Bring your dog, too!
2.0 star property
The price is ￥20,588
￥42,099 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Studio with a View. Bring your dog, too!
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥31,919
￥39,033 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Vacation Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is ￥21,680
￥52,231 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Chester Farmhouse Ski Retreat near Slopes
Interior
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Vacation Home in Dublin

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
10.0 out of 10, Exceptional, (25)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is ￥41,176
￥80,705 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Exterior
Secluded Vermont Chalet w/ Sweeping Mountain Views

Vacation Home in Dover

Secluded Vermont Chalet w/ Sweeping Mountain Views
2.0 star property
The price is ￥21,212
￥79,794 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Secluded Vermont Chalet w/ Sweeping Mountain Views
Property grounds
Family Friendly Hilltop House In Putney Vermont

Vacation Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is ￥25,891
￥47,689 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Family Friendly Hilltop House In Putney Vermont
Terrace/patio
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Chalet in Wardsboro

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is ￥33,534
￥74,553 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is ￥25,423
￥71,253 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Owl's Nest Treehouse

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (14)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
The price is ￥42,892
￥52,631 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Owl's Nest Treehouse
Microwave, oven, stovetop
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Chalet in Wardsboro

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is ￥34,404
￥82,524 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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 Westmoreland Hotel Reviews

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"The room and property in general was amazing. Super comfortable beds, and room plan. Very walkable to many restaurants and attractions in the town center. Easy parking. I wasnt impressed with the "Bistro" that is essentially a starbucks. Also, no free lounge coffee, you have to buy at the Bistro/starbucks. Other than that, it was a really great stay. "
Danielle 1-night trip
Posted 2 days ago
Courtyard by Marriott Keene Downtown

Find out more about Westmoreland

Search for holiday rentals in Westmoreland on Expedia! You can easily find your home rentals, villas, holiday apartments in Westmoreland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Westmoreland!

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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: Visitors like this Westmoreland vacation home rental. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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.