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Check prices for these dates

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

Compare 32 Apartments in Chesterfield with updated reviews, rates, and availability.

Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Property grounds

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
10.0 out of 10, Exceptional, (1)
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (1)
"We stayed here for couple of days. We loved it all! The place is lovely, very clean, spacious, big, and very convenient. The price is very reasonable. The property is beautiful overall! It has orchard trees and a lake. It reminded us the Vermont house in the movie Baby Boom. The location is very convenient too. 10 mins of driving to the MT Snow Ski Resort with lots of winter activities , and also 10 mins of driving to town center of West Dover. We walked in town and shopped in the small...
The price is AED 257
AED 689 total
includes taxes & fees
1 May - 2 May
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Updated Vintage Apartment < 1/2 Mi to Main St
Fridge, microwave, stovetop, dishwasher

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (15)
"Great experience. "
Updated Vintage Apartment < 1/2 Mi to Main St
Lake Whitingham & Mount Snow Area Village Apartment
Fridge, microwave, stovetop, coffee/tea maker

Lake Whitingham & Mount Snow Area Village Apartment

2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
The price is AED 514
AED 1,111 total
includes taxes & fees
24 Apr - 25 Apr
Lake Whitingham & Mount Snow Area Village Apartment
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Exterior

'Red Sweetheart Barn Studio' w/ Mtn & River Views!

9.6 out of 10, Exceptional, (4)
"We enjoyed a few night springtime stay at this beautiful cabin! The view was wonderful, and the accommodations were very nicely decorated. Some things we would love to see improvement on before staying again: there were no washcloths available in the upstairs bathroom, and no garbage can available in the downstairs one. No tissues to be found in the entire space. The bed was extremely uncomfortable, and the pillows as well. We also found fingernail clippings in the sheets, which was problematic,...
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
The Covey House Retreat with InfraRed Sauna
Exterior

The Covey House Retreat with InfraRed Sauna

10.0 out of 10, Exceptional, (3)
"We had an amazing stay, your place is awesome!"
The Covey House Retreat with InfraRed Sauna
Lakefront Orange Vacation Rental - Pet Friendly!
Exterior

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (14)
"Very cozy basement apartment overlooking the water. Quiet road. Owner was very pleasant and accommodating."
Lakefront Orange Vacation Rental - Pet Friendly!
Beautiful Townhouse In Turners Falls!
Property grounds

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (130)
"Our stay made it easy to access the shops and restaurants we needed to go to. Although the main spaces of the living area were clean (living room, bedrooms, kitchen, bathrooms, tubs, showers, toilets, sinks, couch, and beds), we were surprised to see some dust accumulated throughout the unit (on lamps, light fixtures and overhead fans, as well as box fans in the bedrooms) and having to clean the tea kettle and some dishes and glasses before use. We would have given this a 5/5 star stay if we...
Beautiful Townhouse In Turners Falls!
Entire private apartment suite in home with own entrance, views and private gym.
Interior

Entire private apartment suite in home with own entrance, views and private gym.

The price is AED 1,010
AED 1,463 total
includes taxes & fees
29 Apr - 30 Apr
Entire private apartment suite in home with own entrance, views and private gym.
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Exterior

HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley

10.0 out of 10, Exceptional, (4)
"We stayed for the weekend and absolutely loved it- it was huge! Warm and inviting- full kitchen and bathroom, crib in the closet for a wee one. It was so clean and smelled good too- great windows and easy furniture. Bed was superb! Would stay again in a heartbeat. "
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Updated Vintage Apartment < 1/2 Mi to Main St
Apartment (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Interior

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

3.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Interior

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!

3.0 star property
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
1 bedroom, desk, iron/ironing board, free WiFi

Experience New Hampshire Country Life—Your Peaceful Escape Awaits

9.8 out of 10, Exceptional, (30)
"We had a short stay but the hosts were wonderful and gave us a tour when we arrived. The property is gorgeous. Definitely recommend staying here."
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
The Pines Cabin | New Tiny Home Near Mt Snow!
Property grounds

The Pines Cabin | New Tiny Home Near Mt Snow!

The Pines Cabin | New Tiny Home Near Mt Snow!
Fully furnished 2 bdr apartment
Offices

Fully furnished 2 bdr apartment

2.0 star property
Fully furnished 2 bdr apartment
Cozy 1-bedroom apartment in delightful Brattleboro
Fridge, microwave, oven, stovetop

Cozy 1-bedroom apartment in delightful Brattleboro

Cozy 1-bedroom apartment in delightful Brattleboro
Welcome to "Down Under" the Hall's House A peaceful escape in Southern Vermont.
Smart TV, fireplace

Welcome to "Down Under" the Hall's House A peaceful escape in Southern Vermont.

The price is AED 441
AED 581 total
includes taxes & fees
24 Apr - 25 Apr
Welcome to "Down Under" the Hall's House A peaceful escape in Southern Vermont.
'red Sweetheart Barn Studio' w/ Mtn & River Views!
View from property

'red Sweetheart Barn Studio' w/ Mtn & River Views!

3.0 star property
'red Sweetheart Barn Studio' w/ Mtn & River Views!
Spacious 4-bedroom apartment in awesome Guilford with AC
Exterior

Spacious 4-bedroom apartment in awesome Guilford with AC

The price is AED 2,063
AED 2,734 total
includes taxes & fees
30 Apr - 1 May
Spacious 4-bedroom apartment in awesome Guilford with AC
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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Other property types in Chesterfield

GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (49)
"This home is in a beautiful rural setting with rivers and miles of dirt roads. We walked and read and talked and cooked: bliss."
The Jelly Mill-A River Retreat
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (47)
"Stayed twice would stay again"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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.

Frequently asked questions

What's it like to stay at an apartment in Chesterfield?
You might not have many choices centrally in Chesterfield, but Expedia can help you locate lodging options in the area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also filter by similar properties such as vacation homes, condos, or guest houses.
How do you know if an apartment is the best choice for your stay?
An apartment features a kitchen for convenient meals, and is often more spacious than a traditional hotel room. Apartments are a good option for couples who want a more local feel, and also for families wanting the conveniences of home.
What's a favorite apartment for a stay in Chesterfield?
Here are some of the more popular apartments in the area: Studio w/ Trail Access ~ 10 Mi to Brattleboro!: Situated in Vernon, 11.1 mi/17.8 km from the heart of Chesterfield. Includes separate dining areas. Updated Vintage Apartment < 1/2 Mi to Main St: Located 10.6 mi/17.1 km away in Keene. Amenities include private patios. Access to onsite laundry facilities is available on site. Beautiful Townhouse In Turners Falls!: Located in Montague, 20.1 mi/32.3 km away. Includes laundry facilities and private balconies. Access to onsite laundry facilities is available on site. Lakefront Orange Vacation Rental - Pet Friendly!: 21 mi/33.8 km away in Orange. Amenities include fireplaces.
What will the weather be like during my trip to Chesterfield?
Weather is only one factor, but it can really affect your travel plans, especially when you’re planning an extended stay 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 should I see and do in Chesterfield?
While exploring the area, visit family-friendly sights like Brattleboro Bowl, or get outside and enjoy nature at Spofford Lake. Asbury United Methodist Church and Pisgah State Park are other places to visit while you’re in town.
What's the best way to get to and around Chesterfield?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Springfield, VT (VSF-Hartness State), which is located 31.6 mi (50.9 km) away 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, consider renting a car to take in more sights.