A rural landscape with a grassy field, a dirt path, and a hill covered with autumn-colored trees.

Best Resorts in Chesterfield

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Chesterfield resorts

A cozy room with a fireplace, a flat-screen TV mounted above it, and a dining table set with a bottle of champagne, a glass, and a plate of cheese and crackers.

1. Deluxe King Room w/fireplace and separate entrance

Deluxe King Room w/fireplace and separate entrance
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
$343 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
Deluxe King Room w/fireplace and separate entrance
A cozy living room with a fireplace, a dining table set for a meal, and a kitchen in the background.

2. Deluxe King Room w/pull-out love seat and fireplace

Deluxe King Room w/pull-out love seat and fireplace
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfect"
United States
James R.
$343 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
Deluxe King Room w/pull-out love seat and fireplace
A two-story house with a large porch and a pond in front.

3. Deluxe King, kitchenette, fireplace

Deluxe King, kitchenette, fireplace
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"End of season special. Perfect size, fireplace was great on a cold rainy night. Last night restaurant was open for a few weeks."
United States
john L.
$343 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
Deluxe King, kitchenette, fireplace
A two-story house with a large porch and a pond in front.

4. Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Dover
9.4 out of 10, Exceptional, (6 reviews)
"This is a beautiful, large suite in a quaint Vermont town. There are two main rooms: a bedroom with a king bed and a bunk bed, and a separate living room with a fireplace. The main inn also has lounge areas open to guests all night, and is a perfect stay for both families and couples. "
United States
Olivia
$368 nightly
The price is $400
Nov 11 - Nov 12
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
A two-story house with a large porch and a pond in front.

5. Luxury King w/balcony, accessible

Luxury King w/balcony, accessible
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I had a wonderful time at the Inn . our room was beautiful and we had two delicious meals in the restaurant I would definitely recommend this Inn to anyone traveling in southern Vermont."
United States
Kimberley B.
$319 nightly
The price is $346
Nov 11 - Nov 12
Total with taxes and fees
Luxury King w/balcony, accessible
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

6. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$319 nightly
The price is $346
Nov 15 - Nov 16
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
A room with two brown leather armchairs, a wooden coffee table with a bowl and a magazine, and a bed with pillows in the background.

7. Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Dover
10.0 out of 10, Exceptional, (2 reviews)
"The place was clean, cozy and comfortable. The whole estate is beautiful."
United States
Mike T.
$368 nightly
The price is $400
Nov 11 - Nov 12
Total with taxes and fees
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
A two-story house with a large porch and a pond in front.

8. Deluxe King Suite, Living Room w/sofa bed & fireplace

Deluxe King Suite, Living Room w/sofa bed & fireplace
West Dover
10.0 out of 10, Exceptional, (1 review)
"My husband and I really enjoyed the accommodations. Great location with tons do do nearby. The place was so cozy and inviting. Would definitely stay again"
United States
Megan M.
$337 nightly
The price is $366
Nov 12 - Nov 13
Total with taxes and fees
Deluxe King Suite, Living Room w/sofa bed & fireplace
A bedroom with a large bed, a wooden headboard, a nightstand, and a bench.

9. Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
West Dover
8.0 out of 10, Very good, (1 review)
"The inn and grounds were wonderful. Great food at the Sawmill. Wonderful area to explore leading to an all around wonderful time."
United States
Craig C.
$331 nightly
The price is $360
Nov 11 - Nov 12
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

10. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$319 nightly
The price is $346
Nov 11 - Nov 12
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

11. Luxury King with balcony

Luxury King with balcony
West Dover
$319 nightly
The price is $346
Nov 11 - Nov 12
Total with taxes and fees
Luxury King with balcony
A two-story house with a large porch and a pond in front.

12. Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
$307 nightly
The price is $334
Nov 15 - Nov 16
Total with taxes and fees
Deluxe King- 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

13. King with Bunk Bed- 2nd floor in Historic Inn

King with Bunk Bed- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
United States
Forrest W.
$319 nightly
The price is $346
Nov 11 - Nov 12
Total with taxes and fees
King with Bunk Bed- 2nd floor in Historic Inn
A modern bedroom with a bed, bedside tables, a dresser, and a fireplace.

14. Deluxe 2xQueen & fireplace

Deluxe 2xQueen & fireplace
Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful Inn however, the fridge should be lifted off the floor. It’s too low. A small broom and dust pan would be nice to sweep up the dirt that treks in from the dirt parking lot and walk ways. Upgrade full size beds to at least two Queen size beds."
United States
Christina R.
$343 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
Deluxe 2xQueen & fireplace
A hotel room with two beds, a desk, a TV, and a window with a city view.

15. Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very good, (1 review)
$319 nightly
The price is $346
Nov 11 - Nov 12
Total with taxes and fees
Deluxe 2xQueen in Historic Inn
A two-story house with a large porch and a pond in front.

16. Deluxe King, Living Room w/sofa bed & fireplace

Deluxe King, Living Room w/sofa bed & fireplace
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Had a really nice time - the place was lovely. They had some on property activities and were very close to the mountain. We had a great time and would definitely stay here again if back in the area!"
United States
Taylor G.
$343 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
Deluxe King, Living Room w/sofa bed & fireplace
A two-story house with a large porch and a pond in front.

17. Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"
United States
Jessica
$331 nightly
The price is $360
Nov 11 - Nov 12
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
A hotel room with two single beds, a wooden headboard, a small bedside table, and a nightstand with a lamp.

18. Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"Everything was just fantastic! Everyone was friendly and accommodating. Owners were so nice! Property is amazing and a great location to Mount Snow. Can not go wrong with this spot."
United States
Brendan M.
$319 nightly
The price is $346
Nov 11 - Nov 12
Total with taxes and fees
Deluxe 2xQueen- 2nd floor in Historic Inn
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

19. Deluxe Queen Suite with pull-out love seat, private entrance

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
$343 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
Deluxe Queen Suite with pull-out love seat, private entrance
A cozy room with a fireplace, wooden beams, a bookshelf, and a television.

20. Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Dover
9.8 out of 10, Exceptional, (7 reviews)
"My husband and I stayed here so we could ride Mt Snow for a few days. The place is wonderful! All staff is incredibly helpful and friendly, the food and cocktails in their restaurant are phenomenal, the landscape and accommodation are beautiful. We will definitely be back."
United States
Sydney W.
$404 nightly
The price is $440
Nov 11 - Nov 12
Total with taxes and fees
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
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 Chesterfield Hotel Reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"The only part wrong was having difficulty with the door card. Had to get assistance several times. Besides that no complaints"
lillian 1-night trip
Posted 6 hours ago
Days Inn by Wyndham Keene NH

Find out more about Chesterfield

Chesterfield Resorts information

Number of reviews
43
Accommodation
23 Resorts
Lowest Price
$334
Highest Price
$440

Frequently asked questions

What can I expect from a resort vacation in Chesterfield?
Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you want for your trip from tasty dining options to activities and shopping. Browse the resort options in the area and discover the one that's best for you, whether you envision yourself sitting down to fine dining or heading to the spa for a deep-tissue massage.
What's a favorite resort in Chesterfield?
Our highest-rated resorts around Chesterfield: King with Bunk Bed- 2nd floor in Historic Inn - Only a 5-minute walk from Green Mountain National Forest. 19.7 mi (31.6 km) from Chesterfield. Features a car charging station. Deluxe King Room w/pull-out love seat and fireplace - Only a 5-minute walk from Green Mountain National Forest. 19.7 mi (31.6 km) from Chesterfield. Has a car charging station, a bar, and a hot tub. Deluxe King Room w/fireplace and separate entrance - Situated just a 5-minute walk from Green Mountain National Forest. 19.6 mi (31.6 km) from Chesterfield. Enjoy the a car charging station. Deluxe 2xQueen- 2nd floor in Historic Inn - Only a 5-minute walk from Green Mountain National Forest. 19.7 mi (31.6 km) from Chesterfield. Amenities include a car charging station. Luxury King Suite, Living Room w/sofa bed and jacuzzi tub - Only a 5-minute walk from Green Mountain National Forest. 19.7 mi (31.6 km) from Chesterfield. Access to a car charging station.
What can I do in Chesterfield?
Asbury United Methodist Church, Pisgah State Park, and Chesterfield Town Hall are a few of the interesting sights to visit. In the area, other attractions include Spofford Lake and Madame Sherri Forest.
What's the weather like in Chesterfield?
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, November, and February, with each month seeing an average of 9 inches of snowfall.
What's the best way to get to and around Chesterfield?
Fly into Springfield, VT (VSF-Hartness State), which is located 31.6 mi (50.9 km) away from the heart of the city. Otherwise, you can search for flights to 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 a rental car for your journey.

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