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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
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21 Rab. I - 23 Rab. I
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18 Rab. II - 20 Rab. II

Compare 26 Apartments in Chesterfield with updated reviews, rates, and availability.

Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Exterior

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

3.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
The Covey House Retreat with InfraRed Sauna
Room

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
Lake Whitingham & Mount Snow Area Village Apartment
Living Room

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 SAR 525
SAR 1,134 total
includes taxes & fees
24 Feb - 25 Feb
Lake Whitingham & Mount Snow Area Village Apartment
Lakefront Orange Vacation Rental - Pet Friendly!
Orange Vacation Rental | 1BR | 1BA | 902 Sq Ft | Access Only By Stairs

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (12)
"Very cozy basement apartment overlooking the water. Quiet road. Owner was very pleasant and accommodating."
Lakefront Orange Vacation Rental - Pet Friendly!
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Vernon Vacation Rental | Studio | 1BA | Steps Required | 280 Sq Ft

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Updated Vintage Apartment < 1/2 Mi to Main St
Keene Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Steps Required for Entry

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (12)
"We enjoyed our long weekend visit to Keene, NH and appreciated Hidden Gem. It was great to have such a well equipped kitchen for cooking together with fresh local foods from the nearby Monadnock Co-op. Hidden Gem was very clean and comfortable. We had 11 inches of snow overnight and the porch steps, sidewalk and driveway were cleared for us early so we could make our plane on time. Our host Sarah was helpful with any questions and needs. We would love to stay again when our travels take us back...
Updated Vintage Apartment < 1/2 Mi to Main St
Entire private apartment suite in home with own entrance, views and private gym.
Guest suite entrance and patio area with outdoor grill.

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

The price is SAR 1,031
SAR 1,497 total
includes taxes & fees
24 Feb - 25 Feb
Entire private apartment suite in home with own entrance, views and private gym.
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
Westminster Vacation Rental | Studio | 1BA | Stairs Required | 500 Sq Ft

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

10.0 out of 10, Exceptional, (3)
"It was cozy and beautiful and very inviting loved every part"
'Red Sweetheart Barn Studio' w/ Mtn & River Views!
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
Living area

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
Living area

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Experience New Hampshire Country Life—Your Peaceful Escape Awaits
Living area

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

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

3.0 star property
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Foxglove Tiny House - a modern tiny getaway
Welcome to Foxglove Tiny House, your luxury tiny getaway in Jamaica, VT!

Foxglove Tiny House - a modern tiny getaway

Foxglove Tiny House - a modern tiny getaway
Cozy 1-bedroom apartment in delightful Brattleboro
Living area

Cozy 1-bedroom apartment in delightful Brattleboro

Cozy 1-bedroom apartment in delightful Brattleboro
'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!
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
Living area

Relaxing Mountain Refuge: 4 Miles to Mt Snow!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing stay, great hosts, will be back here next time in the area"
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
Large Elegant Historic 2BR, Walk to restaurants!
Table is made from reclaimed barn wood and great for a large dinner.

Large Elegant Historic 2BR, Walk to restaurants!

Large Elegant Historic 2BR, Walk to restaurants!
The Pines Cabin | New Tiny Home Near Mt Snow!

The Pines Cabin | New Tiny Home Near Mt Snow!

The Pines Cabin | New Tiny Home Near Mt Snow!
Maple Hollow Mountain Hideaway
Bathroom

Maple Hollow Mountain Hideaway

Maple Hollow Mountain Hideaway
Riverledge Farm, Unit 2.5
Interior

Riverledge Farm, Unit 2.5

Riverledge Farm, Unit 2.5
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

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

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

8.8 out of 10, Excellent, (45)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Winter wonderland!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Beautiful and peaceful, great house for a winter getaway with the family. We loved the yard and location. Grab your groceries on the way up, and enjoy the amazing house with your crew, (And dog too) "
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
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: Lakefront Orange Vacation Rental - Pet Friendly!: Situated in Orange, 21 mi/33.8 km from the heart of Chesterfield. Includes fireplaces. Beautiful Townhouse In Turners Falls!: Located 20.1 mi/32.3 km away in Turners Falls. Laundry facilities and private balconies are included. Entire private apartment suite in home with own entrance, views and private gym.: Located 12.2 mi/19.7 km away in Keene. Free WiFi, private patios, and fireplaces are included. Access to a fitness center is available on site.
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 Pisgah State Park. Asbury United Methodist Church and Chesterfield Town Hall 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.