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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 Charlestown 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
Charlie Chaplin Suite | Individually decorated, individually furnished, blackout drapes
Rosewood Country Inn

Rosewood Country Inn

3.0 star property
Bradford
9.8 out of 10, Exceptional, (90)
"Comfortable clean rooms and an exceptional breakfast ."
United States
Mark
The price is AED 680
AED 738 total
includes taxes & fees
11 Dec - 12 Dec
Rosewood Country Inn
Property entrance
Follansbee Inn

Follansbee Inn

3.0 star property
North Sutton
9.6 out of 10, Exceptional, (91)
"My mom and I stayed there back in September for a weekend and had a wonderful stay. The inn was so lovely with a beautiful lake across the street. The breakfast provided each morning was top-notch! If I am ever back in the area, I will certainly stay there again!"
United States
Kimberly
The price is AED 645
AED 700 total
includes taxes & fees
10 Dec - 11 Dec
Follansbee Inn
Kayaking
Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain

2.5 star property
Londonderry
9.2 out of 10, Wonderful, (112)
"Lovely pleasant stay. "
United States
Heather
The price is AED 657
AED 723 total
includes taxes & fees
4 Jan - 5 January 2026
Blue Gentian Lodge at Magic Mountain
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AED 713
AED 778 total
includes taxes & fees
10 Dec - 11 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 AED 694
AED 757 total
includes taxes & fees
10 Dec - 11 Dec
Windham Hill Inn
Game room
Dexter's Inn

Dexter's Inn

3.0 star property
Sunapee
8.8 out of 10, Excellent, (70)
"This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. "
United States
Lisa
The price is AED 964
AED 1,046 total
includes taxes & fees
10 Dec - 11 Dec
Dexter's 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
11 Dec - 12 Dec
Room in Historic Inn! 20 Minutes to Okemo!
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
10 Dec - 11 Dec
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
The price is AED 996
AED 1,085 total
includes taxes & fees
17 Dec - 18 Dec
Echo Lake 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)
"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
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)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is AED 878
AED 1,255 total
includes taxes & fees
14 Dec - 15 Dec
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.
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Top Charlestown Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 3 days ago
Pointe at Castle Hill Resort

Frequently asked questions

Searching for B&Bs in Charlestown?
Whether you're passing through town and are looking for an accommodation that's small and charming, or you're traveling solo and hoping to make some connections, B&Bs can be a great choice for many types of vacationers. While you're here, you can get to know Charlestown by exploring its natural beauty. Consider a stop by Swan Commons and Connecticut River State Park.
Why consider B&Bs instead of traditional hotels?
With attentive service, opportunities to meet guests from other places, and of course a full breakfast to start the day, B&Bs all have a unique environment.
What are the top B&Bs in Charlestown?
Here are some B&Bs in the surrounding area: Windham Hill Inn: 8 rooms. 17 mi (27.4 km) from the downtown core. Enjoy the outdoor pool and unique décor. Blue Gentian Lodge at Magic Mountain: 13 rooms. 17.7 mi (28.5 km) from the heart of downtown. Enjoy the free buffet breakfast and spa.
What's the best time of year to book my B&B in Charlestown?
When you're dreaming of a stay in Charlestown, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Charlestown are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Charlestown?
When you want to spend some time in the great outdoors, Connecticut River and Swan Commons are some notable spots. You might put Charlestown Town Hall and The Fort at No.4 Open Air Museum on your list if you want to see more of the area.
How can I get to and around Charlestown?
Planning your excursions in and around Charlestown is easier with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 8.7 mi (14.1 km) away from the heart of the city. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 27.3 mi (44 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.