Westmoreland Holiday Rentals

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Holiday Rentals in Westmoreland

Cabin in Newfane

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 AU$387
includes taxes & fees
11 Dec - 12 Dec
Wellness Getaway with a Personal Sauna, and Private River Beach!

Apartment in Whitingham

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 AU$465
includes taxes & fees
9 Dec - 10 Dec
Lake Whitingham & Mount Snow Area Village Apartment

Cabin in Fitzwilliam

10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is AU$317
includes taxes & fees
7 Dec - 8 Dec
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Apartment in Dover

9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is AU$412
includes taxes & fees
11 Dec - 12 Dec
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Holiday Home in Newport

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 AU$567
includes taxes & fees
8 Dec - 9 Dec
Lake Front Family Friendly Escape

Chalet in Wardsboro

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 AU$714
includes taxes & fees
9 Dec - 10 Dec
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Chalet in Dover

9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is AU$685
includes taxes & fees
15 Dec - 16 Dec
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Chalet in Wardsboro

10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is AU$591
includes taxes & fees
8 Dec - 9 Dec
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Chalet in East Dover

9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AU$606
includes taxes & fees
7 Dec - 8 Dec
Mountain Chalet mins from Mt Snow Skiing/hiking

Cottage in Walpole

10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is AU$381
includes taxes & fees
7 Dec - 8 Dec
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Chalet in West Dover

10.0 out of 10, Exceptional, (20)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
The price is AU$854
includes taxes & fees
10 Dec - 11 Dec
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow

Holiday Home in Stoddard

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 AU$710
includes taxes & fees
8 Dec - 9 Dec
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Holiday Home in Keene

9.6 out of 10, Exceptional, (21)
"Nice house in a nice location. "
United States
Rob B.
The price is AU$422
includes taxes & fees
7 Dec - 8 Dec
Downtown Hot Tub Escape

Holiday Home in Putney

9.4 out of 10, Exceptional, (57)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is AU$431
includes taxes & fees
8 Dec - 9 Dec
Family Friendly Hilltop House In Putney Vermont

Cabin in Grafton

9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is AU$557
includes taxes & fees
15 Dec - 16 Dec
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Holiday Home in Chester Depot

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is AU$309
includes taxes & fees
8 Dec - 9 Dec
Whimsical Room & Private Bathroom in Historic Inn

Apartment in Dover

10.0 out of 10, Exceptional, (4)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is AU$313
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cabin in Alstead

10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is AU$510
includes taxes & fees
14 Dec - 15 Dec
Owl's Nest Treehouse

Holiday Home in Guilford

10.0 out of 10, Exceptional, (1)
"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."
United States
Grant D.
The price is AU$640
includes taxes & fees
16 Dec - 17 Dec
Stunning Glass House nestled in the Vermont wilderness!

Chalet in Dover

2.0 star property
9.8 out of 10, Exceptional, (6)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
The price is AU$1,279
includes taxes & fees
10 Dec - 11 Dec
Private cabin: 7 mins to slopes, wood fireplace
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

Find out more about Westmoreland

Everything you need to know about Westmoreland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westmoreland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westmoreland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westmoreland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westmoreland holiday rentals we have selected for you start as low as AU$412 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westmoreland rentals

At Expedia, we put the best Westmoreland holiday 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 holiday.

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 holiday rental in Westmoreland?

Yes, there are holiday rentals close to the most popular sights in Westmoreland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : This holiday home rental outside of Westmoreland is located in the mountains, and has a fireplace, a patio and laundry facilities 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What’s there to see and do in Westmoreland?

Explore the area and family-friendly sights such as Scott Farm Orchard, 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 wider area.

What’s a holiday rental in Westmoreland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westmoreland. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.