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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 Whitingham 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
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
Front of property
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

2.0 star property
Rowe
The price is AED 547
AED 578 total
includes taxes & fees
11 Dec - 12 Dec
UU Rowe Camp and Conference Center
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
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
Adams
9.0 out of 10, Wonderful, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is AED 638
AED 713 total
includes taxes & fees
11 Dec - 12 Dec
The Trail in Adams - Berkshires’ Art Hotel
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is AED 790
AED 835 total
includes taxes & fees
7 Jan - 8 January 2026
Harbour House 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
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn

The Four Chimneys Inn

4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
The Four Chimneys Inn
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
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
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
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.
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 Whitingham Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. "
Stacey 1-night trip
Posted 3 days ago
The Williams Inn

Frequently asked questions

Searching for B&Bs in Whitingham?
If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your trip. When you want to explore some attractions in town, Harriman Reservoir and Deerfield River are worth a stop.
Why would you choose B&Bs instead of traditional hotels?
With attentive service, opportunities to interact with the owner, and of course a full breakfast to start the day, B&Bs all have a unique setting.
What are the best B&Bs in Whitingham?
Below are some B&Bs in the area: Deerfield Valley Inn: 9 rooms. 10.5 mi (16.9 km) from the heart of Whitingham. Enjoy the unique décor and fireplace in the lobby. Four Columns Inn: 15 rooms. 17.9 mi (28.8 km) from the downtown core. Enjoy the unique décor and coffee shop. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. Situated 16.6 mi (26.7 km) from the heart of Whitingham. Enjoy the unique décor and arcade game room. Big Bears Lodge: 24 rooms. 11.7 mi (18.8 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. The Nutmeg: 14 rooms. Located 5.7 mi (9.1 km) from the core of Whitingham. Enjoy the free cooked breakfast and outdoor pool.
When should I stay at a B&B in Whitingham?
When you're dreaming of a getaway to Whitingham, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Whitingham are January, March, November, and February, with each month seeing an average of 9 inches of snowfall.
What is there to do in Whitingham?
Spend some time exploring Harriman Reservoir and Deerfield River if you're hoping to see some of the area's natural features. You might check out Green Mountain National Forest if you have time to see more of the area.
How can I get to and around Whitingham?
Mapping out your trip in and around Whitingham is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 32.6 mi (52.4 km) away from the heart of the city. If you'd like to explore around the area, you may want to rent a car for your trip.