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Compare 25 Apartments in Chesterfield with updated reviews, rates, and availability.

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
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 Garden Apartment 2 BR, AC & WiFi
Living Room

Lake Whitingham & Mount Snow Area Village Garden Apartment 2 BR, AC & WiFi

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."
Lake Whitingham & Mount Snow Area Village Garden Apartment 2 BR, AC & WiFi
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, (11)
"Great host communication, everything we needed, unexpected extras (like dog treats), and a beautiful view. Would gladly stay again!"
Lakefront Orange Vacation Rental - Pet Friendly!
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, (11)
"This property was just as expected and Close to top notch restaurants. Kitchen was well equipped and I was able to bake a few casseroles for our family we were visiting.The area was nice and quiet. Will visit again."
Updated Vintage Apartment < 1/2 Mi to Main St
'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
1 BR Apt in Wilmington
Exterior detail

1 BR Apt in Wilmington

10.0 out of 10, Exceptional, (1)
"Clean and comfy and near the mtn!"
The price is SAR 1,078
SAR 1,626 total
includes taxes & fees
31 Dec - 1 January 2025
1 BR Apt in Wilmington
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
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!
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 1,033
SAR 1,508 total
includes taxes & fees
25 Dec - 26 Dec
Entire private apartment suite in home with own entrance, views and private gym.
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!
'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!
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
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
Spacious 2BR w/ large loft, Deck, great location
Open comfy space with wide floor boards and spiral access to the large loft.

Spacious 2BR w/ large loft, Deck, great location

10.0 out of 10, Exceptional, (1)
"Rich and Nicky are premier host in my book. They were so responsive with any inquiry and so helpful with area advice. Loved being able to walk to The Tavern and Sawmill for dinner. The house is one of the best equipped I’ve ever stayed in, high end appliances and comfortable furniture and beds. We will return."
Spacious 2BR w/ large loft, Deck, great location
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

Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Hilltop Home with Great Views
Exterior

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great 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 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. In the larger area, you’ll find Asbury United Methodist Church and Spofford Lake.
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.