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Check prices for these dates

Next weekend
12 Dec - 14 Dec
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19 Dec - 21 Dec
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2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Jamaica

Lounge
Bromley View Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (401)
"Overall a decent stay."
United States
Libin
Bromley View Inn
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (13)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
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 SAR 544
SAR 598 total
includes taxes & fees
2 Dec - 3 Dec
Colonel Williams 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 SAR 880
SAR 968 total
includes taxes & fees
1 Jan - 2 January 2026
Inn on Putney Road
Property grounds
The Inn at Manchester

The Inn at Manchester

3.5 star property
Manchester
10.0 out of 10, Exceptional, (280)
"Great establishment "
United States
Brenda
The price is SAR 619
SAR 681 total
includes taxes & fees
4 Dec - 5 Dec
The Inn at Manchester
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is SAR 724
SAR 797 total
includes taxes & fees
2 Dec - 3 Dec
The Inn at Ormsby Hill
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 SAR 450
SAR 723 total
includes taxes & fees
2 Dec - 3 Dec
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, (194)
"Relaxing stay with great hiking nearby"
United States
Charlotte
The price is SAR 635
SAR 720 total
includes taxes & fees
3 Dec - 4 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 SAR 621
SAR 683 total
includes taxes & fees
4 Dec - 5 Dec
The Nutmeg
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 SAR 626
SAR 688 total
includes taxes & fees
2 Dec - 3 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
Property grounds
Zen 10, relax and retreat in the heart of Vermont

Zen 10, relax and retreat in the heart of Vermont

Manchester
10.0 out of 10, Exceptional, (1)
"Very nice and relaxing location"
United States
Jennifer C.
The price is SAR 295
SAR 513 total
includes taxes & fees
2 Dec - 3 Dec
Zen 10, relax and retreat in the heart of Vermont
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is SAR 713
SAR 777 total
includes taxes & fees
15 Dec - 16 Dec
Stone Hearth Inn and Eatery
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 SAR 667
SAR 727 total
includes taxes & fees
10 Dec - 11 Dec
Windham Hill Inn
Front of property
Hill Farm Inn

Hill Farm Inn

4.0 star property
Arlington
9.6 out of 10, Exceptional, (172)
"This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation."
United States
Kenneth
The price is SAR 773
SAR 1,687 total
includes taxes & fees
14 Dec - 15 Dec
Hill Farm Inn
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 SAR 938
SAR 1,032 total
includes taxes & fees
4 Dec - 5 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 SAR 446
SAR 740 total
includes taxes & fees
2 Dec - 3 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
The price is SAR 583
SAR 745 total
includes taxes & fees
4 Dec - 5 Dec
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 SAR 1,130
SAR 1,226 total
includes taxes & fees
3 Dec - 4 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 SAR 746
SAR 821 total
includes taxes & fees
21 Dec - 22 Dec
Deerhill 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.
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Top Jamaica Hotel Reviews

The Covered Bridge Inn

The Covered Bridge Inn

10/10 Excellent
"Room very nice, comfortable clean "
Harlan 1-night trip
Posted 2 days ago
The Covered Bridge Inn

Frequently asked questions

Searching for B&Bs in Jamaica?
If you want to find a place to stay with fewer rooms than a hotel and a more personalized environment, a bed and breakfast might be a great fit for your getaway to Jamaica. When you want to explore some attractions in town, Jamaica State Park and Green Mountain National Forest are worth a stop.
How do you know if a B&B is the right choice for your stay?
With attentive service, an atmosphere suited to mingling with other guests, and of course a full breakfast, B&Bs provide a unique environment.
What are the best bed and breakfasts in Jamaica?
Here are some well-liked B&Bs in the area: Deerfield Valley Inn: 9 rooms. 11.7 mi (18.9 km) from the heart of Jamaica. Enjoy the unique décor and fireplace in the lobby. The Inn at Manchester: 18 rooms. 15.4 mi (24.7 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. Four Columns Inn: 15 rooms. Situated 10 mi (16.1 km) from the heart of Jamaica. Enjoy the unique décor and coffee shop. Bromley View Inn: 16 rooms. 9.6 mi (15.5 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby. The Inn at Ormsby Hill: 10 rooms. Located 16 mi (25.7 km) from the core of Jamaica. Enjoy the free full breakfast and designer toiletries.
When should I book my B&B in Jamaica?
When you're dreaming of a escape to Jamaica, year-round temperatures and rainfall may be important factors to consider. 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 24°F. The snowiest months in Jamaica are January, March, November, and February, with each month seeing an average of 9 inches of snowfall.
What is there to do in Jamaica?
When you want to spend some time in the great outdoors, Green Mountain National Forest and Winhall River are some notable spots. You might put Jamaica State Park and Ball Mountain Dam on your list if you want to see more of the area.
How can I get to and around Jamaica?
You can map out your trip in and around Jamaica ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 21.1 mi (34 km) away from the heart of the city. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 30.7 mi (49.4 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.