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

Search Resort Hotels in Chesterfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe King Room w/fireplace and separate entrance
A hotel room with two single beds, a wooden headboard, a small bedside table, and a nightstand with a lamp.

2. 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.
The price is CA $421
CA $672 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe 2xQueen- 2nd floor in Historic Inn
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.
The price is CA $503
CA $775 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is CA $503
CA $775 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
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.

5. 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.
The price is CA $503
CA $763 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
A cozy living room with a fireplace, a dining table set for a meal, and a kitchen in the background.

6. 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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe King Room w/pull-out love seat and fireplace
A modern bedroom with a bed, bedside tables, a dresser, and a fireplace.

7. 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.
The price is CA $421
CA $672 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe 2xQueen & fireplace
A two-story house with a large porch and a pond in front.

8. 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
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
A two-story house with a large porch and a pond in front.

9. 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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Luxury King w/balcony, accessible
A two-story house with a large porch and a pond in front.

10. 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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
King with Bunk Bed- 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

11. 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.
The price is CA $503
CA $775 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe King Suite, Living Room w/sofa bed & fireplace
A hotel room with two beds, a desk, a TV, and a window with a city view.

12. Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very good, (1 review)
The price is CA $421
CA $672 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe 2xQueen in Historic Inn
A two-story house with a large porch and a pond in front.

13. 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.
The price is CA $503
CA $775 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe King, Living Room w/sofa bed & fireplace
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

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

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
The price is CA $421
CA $672 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe Queen Suite with pull-out love seat, private entrance
A cozy room with a fireplace, wooden beams, a bookshelf, and a television.

15. 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.
The price is CA $519
CA $794 total
includes taxes & fees
Sep 27 - Sep 28
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
A bedroom with a large bed, a wooden headboard, a nightstand, and a bench.

16. 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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
A two-story house with a large porch and a pond in front.

17. Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
The price is CA $454
CA $713 total
includes taxes & fees
Sep 28 - Sep 29
Deluxe King- 2nd floor in Historic Inn
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

18. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe King - 2nd floor in Historic Inn
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

19. Luxury King with balcony

Luxury King with balcony
West Dover
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Luxury King with balcony
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

20. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
The price is CA $454
CA $713 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe King - 2nd floor 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Chesterfield Resorts information

Number of reviews
Accommodation
 Resorts
Lowest Price
Highest Price

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.

Explore a world of travel with Expedia