Book Westmoreland Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 21 - Nov 23
In two weeks
Nov 28 - Nov 30
In one month
Dec 12 - Dec 14
In two months
Jan 9 - Jan 11

B&B in Westmoreland

Exclusive Room | Premium bedding, Tempur-Pedic beds, individually decorated
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.6 out of 10, Exceptional, (10)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$123 nightly
The price is $135
Nov 22 - Nov 23
Total with taxes and fees
Four Columns 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)
"This BNB is delightful. Great location and easy to find in town. Lovely house, room, easy check in, and the owner was great. The owner was there when we checked in and gave us a tour and recommendations for dinner in town. Downtown is just darling and easy walking around the town square. Dinner in town was excellent as well. I would highly recommend a stay here to anyone. "
United States
Tina
$168 nightly
The price is $183
Dec 14 - Dec 15
Total with taxes and fees
The Carriage Barn Inn
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (338)
"Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay."
Canada
Carolyn
$158 nightly
The price is $173
Nov 19 - Nov 20
Total with taxes and fees
Colonel Williams Inn
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (84)
"We had a lovely time staying here. "
United States
Jeff
$94 nightly
The price is $104
Nov 23 - Nov 24
Total with taxes and fees
Deerfield Valley Inn
TV
The Nutmeg

The Nutmeg

3.5 star property
Wilmington
9.4 out of 10, Exceptional, (412)
"This place is very nice Very old. The shower is very small very hard to move. They need a better assortment of pillows I woke up with a stiff neck and back ache. The breakfast was very good made fresh. The staff is very friendly and kind. Overall a nice little inn."
United States
Carl
$169 nightly
The price is $186
Nov 23 - Nov 24
Total with taxes and fees
The Nutmeg
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, (17)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
United States
Nevets
$135 nightly
The price is $151
Nov 17 - Nov 18
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
Porch
The Wilmington Inn

The Wilmington Inn

3.5 star property
Wilmington
10.0 out of 10, Exceptional, (193)
"The Wilminton Inn is one of the best B&B's that my wife and I have stayed. The owners are super friendly, the place is very clean with a bar and comfortable family area. Breakfast was great. We highly recommend the Wilmington Inn."
United States
Charles
$208 nightly
The price is $228
Nov 30 - Dec 1
Total with taxes and fees
The Wilmington Inn
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (273)
"The owners are the best. Wonderful place, made with love. "
United States
Adele
$148 nightly
The price is $161
Nov 17 - Nov 18
Total with taxes and fees
Monadnock 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
$267 nightly
The price is $294
Nov 17 - Nov 18
Total with taxes and fees
Inn on Putney Road
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (172)
"The property was wonderful and the hosts exceptional❤️"
United States
Susan
$175 nightly
The price is $185
Dec 14 - Dec 15
Total with taxes and fees
Centennial House
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"We loved our stay! Very welcoming and cozy. The breakfast was delicious. Will definitely come back to stay here again!"
United States
Wiley
$245 nightly
The price is $270
Nov 19 - Nov 20
Total with taxes and fees
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)
"Yes, wonderful location and stay"
United States
Sharon
$144 nightly
The price is $161
Nov 17 - Nov 18
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Exterior
The Engel House

The Engel House

3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"Warm and inviting atmosphere. Great location. "
United States
Diane
$193 nightly
The price is $211
Nov 17 - Nov 18
Total with taxes and fees
The Engel House
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
$189 nightly
The price is $206
Dec 15 - Dec 16
Total with taxes and fees
Windham Hill Inn
Garden
Big Bears Lodge

Big Bears Lodge

3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The property is conveniently located in close proximity to Mt Snow and local restaurants. The staff is friendly. There's a big screen tv room with fireplace and a small sitting room to read or just converse. Rooms are a little dated but clean. Would stay again."
United States
Jonathan
$167 nightly
The price is $183
Dec 1 - Dec 2
Total with taxes and fees
Big Bears Lodge
Exterior
Green River Bridge Inn

Green River Bridge Inn

3.0 star property
Guilford
8.4 out of 10, Very Good, (13)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
United States
Melissa
$258 nightly
The price is $282
Dec 14 - Dec 15
Total with taxes and fees
Green River Bridge Inn
Exterior
Deerhill Inn

Deerhill Inn

3.5 star property
West Dover
9.6 out of 10, Exceptional, (223)
"An excellent stay! Warm and accommodating and helpful in every way. Wonderful breakfast too!"
United States
Clarence
$193 nightly
The price is $213
Nov 25 - Nov 26
Total with taxes and fees
Deerhill Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed."
United States
Susan
$301 nightly
The price is $327
Nov 17 - Nov 18
Total with taxes and fees
Chesterfield Inn
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)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
$202 nightly
The price is $226
Nov 17 - Nov 18
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
$159 nightly
The price is $178
Nov 17 - Nov 18
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Westmoreland Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Staff was outstanding! Informative, kind, engaging, helpful...facility is a wonderful, old building whose history has been respected. Convenient parking lot, and a very walkable area with great restaurants in the area. Looking forward to another stay!"
Alex Ann 4-night trip
Posted 2 days ago
Latchis Hotel

Find out more about Westmoreland

Westmoreland B&B information

Number of reviews
2,121
Accommodation
38 B&B
Lowest Price
$104
Highest Price
$327

Frequently asked questions

What is the nightly rate for a B&B in Westmoreland?
Prices for B&Bs in Westmoreland often vary, but you can find a great deal from $104 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Westmoreland B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Westmoreland?
The best time to book a B&B in Westmoreland is during the peak season from March to May. This vibrant period welcomes travelers eager to experience the blossoming beauty of spring, making it an ideal time for outdoor exploration and sightseeing. Visitors can indulge in activities such as hiking and enjoying the picturesque landscapes that Westmoreland has to offer, all while enjoying mild temperatures typically ranging from the low 40s to mid-70s Fahrenheit.

March is particularly popular, as the area begins to shake off winter's chill, and outdoor enthusiasts can take advantage of the comfortable weather to explore local parks and trails. The scenic surroundings are superb for leisurely strolls or picnics, allowing travelers to fully immerse themselves in the region's natural charm.

For those seeking a more budget-friendly option, consider visiting in December. While this month is outside the main tourist season, it presents a unique opportunity to experience the tranquil beauty of Westmoreland during its quieter days. You may find that the festive atmosphere adds an enchanting touch to your stay, with cozy gatherings and local events to enjoy.
What is the difference between a Westmoreland Bed & Breakfast and a hotel?
Every Westmoreland B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Westmoreland B&Bs.

Explore a world of travel with Expedia