Find a Bed and Breakfast in Chesterfield from CA $144

Browse Select Chesterfield B&B

Colonel Williams Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (268)
"We loved this off-the-beaten-path, classic bed & breakfast a few minutes from Brattleboro on the old stagecoach route. Our view over the pond was stunning, and the breakfast was fresh and ample. The room was quiet, and the bed was very comfortable. My only suggestion would be to bring a small travel light if you would like to read a book in bed, as our room had soft, mellow lighting. "
The price is CA $197
CA $215 total
includes taxes & fees
Jul 7 - Jul 8
Colonel Williams Inn
Centennial House
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (131)
"The property was charming and the hosts wonderful "
The price is CA $273
CA $289 total
includes taxes & fees
Jul 2 - Jul 3
Centennial House
Harvest Barn Inn
Porch
Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (171)
"I had a wonderful stay. Kaelan was an awesome host. great breakfast as well!"
The price is CA $233
CA $254 total
includes taxes & fees
Jun 26 - Jun 27
Harvest Barn Inn
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Deerfield Valley Inn
Exterior
Deerfield Valley Inn
3.0 star property
10.0 out of 10, Exceptional, (3)
"I had an absolutely wonderful stay at Dearfield Valley Inn in West Dover, VT. The charming ambiance, attentive staff, and cozy rooms made for a delightful experience. The inn's picturesque surroundings added to the overall charm, creating a perfect getaway. I highly recommend it for anyone seeking a peaceful and memorable stay in Vermont."
The price is CA $144
CA $186 total
includes taxes & fees
Jun 24 - Jun 25
Deerfield Valley Inn
The Carriage Barn Inn
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (125)
"No real “gardens” but the property is still very pleasant and VERY well located."
The price is CA $292
CA $317 total
includes taxes & fees
Jun 30 - Jul 1
The Carriage Barn Inn
The One Cat B&B
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (70)
"Perfect location near downtown Brattleboro. Convenient, easy walk to shops, restaurants, museums. Pat and Conrad were warm, welcoming hosts. Conrad's homemade bread was delicious. I'm returning in October for his homemade English muffins and for some leaf peeping in the Green Mountains and the White Mountains just across the river. My room was very comfortable, with a comfy loveseat tucked under the corner windows for a perfect reading nook and what was probably the most comfortable bed I've...
The price is CA $274
CA $302 total
includes taxes & fees
Jun 23 - Jun 24
The One Cat B&B
Windham Hill Resort
Romantic Room, 1 King Bed | Mountain view
Windham Hill Resort
3.0 star property
8.2 out of 10, Very good, (27)
"We stayed in the 8-room converted barn. The room very large and a pleasant surprise featuring a great view, soaking tub in the living area, gas fireplace, and a very comfortable king bed. I would give Windham Hill Inn five stars, but I deducted a star because of a clogged bathroom sink, a difficult to control HVAC system, and live and dead bugs in the room. Although somewhat dated, the room was spectacular for the price. "
The price is CA $224
CA $245 total
includes taxes & fees
Jun 23 - Jun 24
Windham Hill Resort
Inn on Putney Road
Exterior
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (39)
"The Inn is charming and beautifully furnished. The gardens are beautiful. The innkeeper and staff were gracious and our room was decked out with complimentary Vermont treats. The breakfast was lavish - muffins, fruit, eggs, potatoes, sausage, freshly ground coffee and fresh-squeezed juice. We only did a quick overnight visit but next time it would be fun to stay longer to take advantage of the game room and the many books."
The price is CA $404
CA $445 total
includes taxes & fees
Jun 25 - Jun 26
Inn on Putney Road
Deerhill Inn
Exterior
Deerhill Inn
3.5 star property
9.6 out of 10, Exceptional, (200)
"I would 100% stay here again! Incredibly caring, attentive, friendly hosts! We stayed in the Orchid room and it was beautiful. Whether it was remembering a small detail of one guest such as lactose intolerance or recommendations of things to do in town, the owners were always willing to help in any way they can. "
The price is CA $240
CA $264 total
includes taxes & fees
Jun 23 - Jun 24
Deerhill Inn
Chesterfield Inn
Lobby
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
The price is CA $413
CA $448 total
includes taxes & fees
Jun 23 - Jun 24
Chesterfield Inn
Four Columns Inn
Deluxe Room | Living area
Four Columns Inn
3.0 star property
8.6 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
The Engel House
Exterior
The Engel House
3.0 star property
9.4 out of 10, Exceptional, (6)
"Last minute reservation for trip to see the eclipse. Very nice a"
The price is CA $214
CA $233 total
includes taxes & fees
Jul 2 - Jul 3
The Engel House
The Brattleboro
Seasonal outdoor pool
The Brattleboro
3.0 star property
10.0 out of 10, Exceptional, (4)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. "
The Brattleboro
Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Private kitchen
Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Deerfield Valley Inn, 5min. to M.Snow Room Entire Inn
Deerfield Valley Inn - Suite Room
Interior
Deerfield Valley Inn - Suite Room
The price is CA $686
CA $931 total
includes taxes & fees
Jun 22 - Jun 23
Deerfield Valley Inn - Suite Room
Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
1 bedroom, WiFi, bed sheets
Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
The price is CA $686
CA $905 total
includes taxes & fees
Jun 23 - Jun 24
Deerfield Valley Inn - Deluxe Room with Fireplace Room 5
Deluxe Room with Fireplace Room 2
1 bedroom, iron/ironing board, WiFi, bed sheets
Deluxe Room with Fireplace Room 2
The price is CA $686
CA $905 total
includes taxes & fees
Jun 22 - Jun 23
Deluxe Room with Fireplace Room 2
Deerfield Valley Inn - Budget Club Room 3
1 bedroom, iron/ironing board, WiFi, bed sheets
Deerfield Valley Inn - Budget Club Room 3
The price is CA $686
CA $905 total
includes taxes & fees
Jun 24 - Jun 25
Deerfield Valley Inn - Budget Club Room 3
Deerfield Valley Inn - Standard Room 7
1 bedroom, iron/ironing board, WiFi, bed sheets
Deerfield Valley Inn - Standard Room 7
The price is CA $686
CA $905 total
includes taxes & fees
Jun 24 - Jun 25
Deerfield Valley Inn - Standard Room 7
Deluxe Room with Fireplace Room 1
1 bedroom, iron/ironing board, WiFi, bed sheets
Deluxe Room with Fireplace Room 1
Deluxe Room with Fireplace Room 1
Don't see what you're looking for?
See all available properties in Chesterfield
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.

Other property types in Chesterfield

Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, (27)
"This cabin is so wonderful. The linens are exquisite and the beds are super comfortable. It is decorated so cute. There is everything you need! My favorite activity was sitting in the wooden rocking chair on the front porch each morning, drinking coffee, listening to nature (frogs, fish), and watching the lovely pond (which is so big it should be called a lake!) The owner responded to all my questions within minutes. You can even have pizza (regular AND gluten free) delivered!! If you visit, you...
Charming Waterfront Log Cabin
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (25)
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (9)
"The grounds were well kept. The house was remodeled and very clean. Lots of room. Equipped with everything you would need. Quiet. Owners were awesome to deal with and easy to get ahold of. I would definitely recommend people to stay there. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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.

Chesterfield B&B information

Number of reviews
935
Accommodation
23 B&B
Lowest Price
CA $144
Highest Price
CA $686

Frequently asked questions

Searching for B&Bs in Chesterfield?
Whether you’re on a family vacation and want a small, cozy place to stay, or you’re a solo traveler hoping to meet fellow tourists, a B&B can be a good choice for many different types of travelers. If your ideal vacation to Chesterfield includes spending lots of time outside, Pisgah State Park is a good spot to enjoy the scenery.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to mingle with other guests, and tasty breakfasts, B&Bs all have a truly one-of-a-kind setting.
What are the top B&Bs in Chesterfield?
Here are some B&Bs in the area: Centennial House: 5 rooms. 13.2 mi (21.2 km) from the heart of Chesterfield. Enjoy the free full breakfast and library. Harvest Barn Inn: 7 rooms. Situated 18.1 mi (29.1 km) from the heart of Chesterfield. Enjoy the free full breakfast and patio area.
What's the best time of year to book my B&B in Chesterfield?
When you’re dreaming of a trip to Chesterfield, 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 Chesterfield are January, March, April, and November, with each month seeing an average of 9 inches of snowfall.
What is there to do in Chesterfield?
When you want to explore some things to do in town, Asbury United Methodist Church and Pisgah State Park are some notable sights to visit. Spofford Lake and Madame Sherri Forest are also some sites to visit if you want to see more of the area.
How can I get to and around Chesterfield?
You can plan your excursions in and around Chesterfield ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 31.6 mi (50.9 km) from the city center. Otherwise, look for flights into Manchester-Boston Regional Airport (MHT), which is 52.3 mi (84.2 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.

Recent Reviews in Chesterfield
Expedia verified reviews

Latchis Hotel

Latchis Hotel

5/5 Excellent
"Beautiful classic hotel!"
A verified traveller stayed at Latchis Hotel
Posted 2 days ago
Latchis Hotel