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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Westmoreland bed & breakfast

Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Porch
Harvest Barn Inn

Harvest Barn Inn

3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is AED 463
AED 503 total
includes taxes & fees
31 Dec - 1 January 2026
The Carriage Barn Inn
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is AED 732
AED 774 total
includes taxes & fees
28 Dec - 29 Dec
Centennial House
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AED 544
AED 598 total
includes taxes & fees
15 Dec - 16 Dec
Colonel Williams Inn
Porch
The Wilmington Inn

The Wilmington Inn

3.5 star property
Wilmington
10.0 out of 10, Exceptional, (195)
"Relaxing stay with great hiking nearby"
United States
Charlotte
The price is AED 587
AED 665 total
includes taxes & fees
12 Dec - 13 Dec
The Wilmington Inn
TV
The Nutmeg

The Nutmeg

3.5 star property
Wilmington
9.4 out of 10, Exceptional, (414)
"This was a beautiful quaint property with delightful and attentive staff. The French toast breakfast was amazing! "
United States
John
The price is AED 621
AED 684 total
includes taxes & fees
15 Dec - 16 Dec
The Nutmeg
Mountain view
Windham Hill Inn

Windham Hill Inn

4.0 star property
West Townshend
8.6 out of 10, Excellent, (37)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
United States
Brandon
The price is AED 694
AED 757 total
includes taxes & fees
1 Jan - 2 January 2026
Windham Hill Inn
Exterior
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is AED 862
AED 948 total
includes taxes & fees
1 Jan - 2 January 2026
Inn on Putney Road
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is AED 441
AED 708 total
includes taxes & fees
14 Dec - 15 Dec
Room in Historic Inn! 20 Minutes to Okemo!
Garden
Big Bears Lodge

Big Bears Lodge

3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is AED 612
AED 674 total
includes taxes & fees
11 Dec - 12 Dec
Big Bears Lodge
Exterior
The Engel House

The Engel House

3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"A very quaint property. The room was comfortable and clean."
United States
Frank
The Engel House
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is AED 900
AED 990 total
includes taxes & fees
28 Dec - 29 Dec
The One Cat B&B
Dining
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Chester Depot
9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
United States
Jacque
The price is AED 437
AED 724 total
includes taxes & fees
11 Dec - 12 Dec
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (86)
"We had a lovely time staying here. "
United States
Jeff
Deerfield Valley Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is AED 1,106
AED 1,200 total
includes taxes & fees
14 Dec - 15 Dec
Chesterfield Inn
Exterior
Deerhill Inn

Deerhill Inn

3.5 star property
West Dover
9.6 out of 10, Exceptional, (224)
"Our hosts Arianne and Scott were very welcoming! The room was very comfortable and the breakfast and our server Cindy were amazing! Definitely recommend Deerhill Inn! "
United States
David
The price is AED 738
AED 812 total
includes taxes & fees
4 Jan - 5 January 2026
Deerhill Inn
Outdoor dining
Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Guilford
The price is AED 1,010
AED 1,296 total
includes taxes & fees
17 Dec - 18 Dec
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is AED 951
AED 1,399 total
includes taxes & fees
3 Jan - 4 January 2026
King & Queen Suite in Historic Inn Circa 1780
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
"Very comfortable and clean."
Christina 1-night trip
Posted 3 days ago
Courtyard by Marriott Keene Downtown

Frequently asked questions

Searching for B&Bs in Westmoreland?
If you want to find a place to stay with fewer rooms than a hotel and a more personalized environment, a B&B might be the perfect option for your vacation to Westmoreland. When you want to explore some of the destination's attractions, Connecticut River is worth a visit.
Why choose a B&B over a traditional hotel room?
Every B&B has a unique charm. Whether it's a picturesque garden or a beautiful dining room, the tiny details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Westmoreland?
Below are some B&Bs in the area: Four Columns Inn: 15 rooms. 11 mi (17.7 km) from the downtown core. Enjoy the unique décor and coffee shop. Centennial House: 5 rooms. Located 18.3 mi (29.5 km) from the core of Westmoreland. Enjoy the free full breakfast and unique décor.
When is the best time to book my B&B in Westmoreland?
When you're dreaming of a trip to Westmoreland, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Westmoreland are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.
What is there to do in Westmoreland?
When you want to explore some things to do in Westmoreland, consider a visit to Connecticut River. You might also consider a trip to sites like Spofford Lake or Chesterfield Gorge Natural Area if you have time to see more of the area.
How can I get to and around Westmoreland?
Mapping out your trip in and around Westmoreland is easy with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 26.6 mi (42.9 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.