Westmoreland Holidays from £795

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

Top Westmoreland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Springfield (VSF)
8.8/10 Excellent! (495 reviews)
I love staying at the Mountaineer. I stay there every time I go to Vermont. The staff is very friendly and welcoming. Parking is very easy good location, central to many restaurants and other amenities. Very nice coffee bar beautiful pool for swimming. great atmosphere. Love the easy check-inprocess. Everything is digital no keys to worry about.

Reviewed on 6 Aug 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Save 100% on your flight
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Springfield (VSF)
9.6/10 Exceptional! (54 reviews)
This is such a charming, historic New England bed and breakfast. The quintessential Vermont experience right in the heart of the quaint village of West Dover. The Innkeeper knows all the people & places around. Homemade breakfast options are delicious, I had the local blueerry waffles. The Blueberry Festival parade passed right in front of the inn. I drank the Inn's coffee in the morning outside on their lawn, on one of the oversized stone seats around the firepit. There are books on the shelves and games in the living room. The Inn is in a perfect location, walking distance - with sidewalks - to multiple restaurants. And just 10 minutes to the town of Wilmington and the GORGEOUS water at Harriman Reservoir or Lake Raponda. There's 2 golf courses a few minutes away. And 2 ski mountains too! This place is super quiet, but close to whatever you might need. The Inn is filled with cozy furnishings, antiques, fireplaces, etc. Lovely lovely, so New England, so Vermont.

Reviewed on 8 Aug 2025

Windham Hill Inn

Windham Hill Inn

4 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Springfield (VSF)
8.4/10 Very Good! (36 reviews)
The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous.

Reviewed on 11 Jul 2025

Chalet 239

Chalet 239

2 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Springfield (VSF)
9.4/10 Exceptional! (70 reviews)
Perfect Chaet!!! Will definitely come back and highly recommend.

Reviewed on 13 Apr 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Springfield (VSF)
8.8/10 Excellent! (211 reviews)
The staff was excellent! The room was clean but terrible! The king size bed was as hard as a rock!! Got very little sleep. The room had sings of water damage in the corner by the window. The TV is in a strange spot to watch from the bed and the cable nut was tripped and would not tighten down. The bathroom door would not shut unless you forced it closed. The shower head leaked unless you turned it off very hard. There was no night stand on one side of the bed making one person putting there stuff on the floor next to the bad. On top of all of this there was an extra $25.00 dollar fee witch I was not expecting for the room. The resort was excellent though and the staff was great. I heated the room!

Reviewed on 1 Aug 2025

Westmoreland Essential Information

Language
English
Currency
U.S dollars
Population
1,850
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Walpole Mountain View Winery, Hooper Golf Club and Walpole Artisans Cooperative

Top hotels in Westmoreland

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is £114 per night from 24 Aug to 25 Aug
£114
24 Aug - 25 Aug
includes taxes & fees
6.6/10 (1,002 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on 28 Jul 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is £100 per night from 4 Sept to 5 Sept
£100
4 Sept - 5 Sept
includes taxes & fees
8/10 Very Good! (859 reviews)
"this is a very nice hotel, and we have stayed before and will stay again, but we will never stay in 212 again, they play music in the lobby and halls 24/7 which is fine, but 212 is right over the lobby and you can hear the drumming all night, it is very irritating, but like I said we have stayed ..."

Reviewed on 4 Aug 2025

Hampton Inn Brattleboro
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is £101 per night from 17 Aug to 18 Aug
£101
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (873 reviews)
"Staff were friendly, room clean and comfortable"

Reviewed on 7 Aug 2025

Keene Elm City Hotel, Ascend Hotel Collection
See all 1,124 properties in Westmoreland
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

Why should I book my Westmoreland holiday with Expedia?
Choose Expedia to plan your next big adventure easily and all in one place. Our insider tip for scoring a terrific deal on a Westmoreland retreat? Bundle your airfares, hotel and/or car hire into a package holiday. Then add a couple of exciting tours and activities. Most bookings also include flexible cancellation policies, so there's no need to panic if you have to switch up your itinerary. Round-the-clock assistance with cancelling and changing your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Westmoreland?
To enjoy the energy of peak season, take off in February, March and May. January, October and December are typically quieter and a good idea if you'd rather escape the crowds. With daytime average temperatures of -5ºC, January is the coolest month in Westmoreland. The warmest month is July, when you can expect averages of 21ºC during the day. Whatever the weather, you'll discover plenty of things to keep you occupied here.
What is the top hotel for my holiday in Westmoreland?
Create unforgettable memories in Westmoreland by choosing Courtyard by Marriott Keene Downtown as your gateway to exploration.
How do I get a cheap holiday to Westmoreland?
Combine your flight and hotel bookings, toss in extras such as activities or a hire car, and save with a Westmoreland holiday. You won't just enjoy superb discounts on your escape — you'll have a world of choice within your reach too. When you book through Expedia, you can choose from more than 400 airlines and 321,000 properties around the world. Your next affordable holiday begins right here, right now! Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Westmoreland holiday?
Offering popular attractions such as Walpole Mountain View Winery and Walpole Artisans Cooperative, a holiday in Westmoreland promises plenty of fun places to visit. Hooper Golf Club and Petes Stand Vegetables are two other sights also worth checking out.
Do I need a visa for my Westmoreland holiday?
Official government websites have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and the purpose of your visit, whether it be for holidays or business, will determine if you'll need a visa for Westmoreland. Also check that your passport is up to date and has a minimum of six months validity remaining after your planned date of return. Do all your travel planning ahead of time to avoid any last-minute surprises.
What should I wear on my Westmoreland holiday?
Though everyone's fashion style is different, it can be useful to have a few guidelines for what to bring on your holiday in Westmoreland. Think about browsing social media before you head off to get inspiration for local fashion trends. Pack your luggage with confidence by looking up the weather conditions in Westmoreland. July brings the warmest temperatures, with daily averages of 21ºC, while January days average -5ºC, making it the coolest time of the year.
What does an Expedia Westmoreland holiday include?
That depends entirely on you. Simply choose from a range of Westmoreland packages, such as a hotel, flight and hire car. You can also book a flight and a hotel, or a flight with a car hire. Once you've made your booking, add on the fun stuff like experiences and tours. Whatever your dream Westmoreland getaway looks like, you're sure to save! Expedia features all types of properties, with the most sought after in Westmoreland being private holiday homes and cottages. With Expedia, you'll always have the flexibility and freedom to customise your holiday however you like.
Does Expedia offer Book Now, Pay Later Westmoreland holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway a little easier on the wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more cash to play with while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that fits into your budget. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient payment plans. If paying over multiple transactions sounds right for you, choose this option during the checkout process.
  • No-deposit holidays: Clicking the "book now" button is much easier with this plan. With no deposit required for your holiday, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Westmoreland Expedia holiday?
Most definitely. Expedia has more than 400 partner airlines to select from around the world. With all that choice at your fingertips, finding the right carrier to whisk you away to Westmoreland shouldn't be hard.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.