Search Apartments in Chesterfield

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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

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, (9)
"It’s a wonderful place to stay!!"
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
9.8 out of 10, Exceptional, (8)
"Place is great! Pricing is deceiving…fees were double the actual rent. Small ramp from kitchen to living room is dangerous!"
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!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
"The Murdock Suite @ The Large House"
Interior
"The Murdock Suite @ The Large House"
9.6 out of 10, Exceptional, (4)
"This was a great place to stay for an extended weekend while attending a family event. Swanzey is literally 5 miles from from Keene, NH. The 2 bed upstairs unit offered plenty of seating in both the (very comfortable) living room and the nice sized (6 seat) dining room. The bedrooms were nearly identical and the Americana decor is fresh. The mattresses were comfortable. Having laundry available was a great relief. The finishes are beautiful and the basic supplies were “spot on”. The owner...
"The Murdock Suite @ The Large House"
Sunny, convenient 4-Bed Family Base w/Balcony: Fast WiFi, WFH, 15 min to ski!
Sunny open-concept family apartment
Sunny, convenient 4-Bed Family Base w/Balcony: Fast WiFi, WFH, 15 min to ski!
10.0 out of 10, Exceptional, (6)
"My family has loved staying here two years in a row for a ski weekend. Perfect distance to Mt Snow and Stratton. Great living room/kitchen setup to hang after a full day of skiing"
Sunny, convenient 4-Bed Family Base w/Balcony: Fast WiFi, WFH, 15 min to ski!
Studio Close to Downtown w/ Trail Access
Sofa turns into a comfy sleeper (for one person, twin size)
Studio Close to Downtown w/ Trail Access
Studio Close to Downtown w/ Trail Access
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, (1)
"The apartment is charming. Very clean, with everything I needed for a nice stay. The bed was very comfortable and the building was very quiet. I can’t wait to go back."
HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley
1 BR Apt in Wilmington
Exterior
1 BR Apt in Wilmington
10.0 out of 10, Exceptional, (1)
"Clean and comfy and near the mtn!"
1 BR Apt in Wilmington
The Covey House 2BR Apt
Master bedroom, queen bed, overlooks village green. Large closet and dresser
The Covey House 2BR Apt
10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed the spaciousness of this apartment. Plentiful amenities make it feel like a home away from home. Very comfortable beds. Multiple tables and abundant chairs for meals and board games. Lots of closet space. We cooked many of our meals in and enjoyed them in the comfort of the apartment which includes a full dining room. The hosts were attentive, helpful, and friendly. We’re looking forward to returning again in a couple months."
The Covey House 2BR Apt
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!
The Covey House Retreat with InfraRed Sauna
Room
The Covey House Retreat with InfraRed Sauna
The Covey House Retreat with InfraRed Sauna
'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
Interior
Maple Hollow Mountain Hideaway
Maple Hollow Mountain Hideaway
Riverledge Farm, Unit 2.5
View from property
Riverledge Farm, Unit 2.5
Riverledge Farm, Unit 2.5
Lakefront Orange Vacation Rental - Pet Friendly!
Living area
Lakefront Orange Vacation Rental - Pet Friendly!
3.0 star property
Lakefront Orange Vacation Rental - Pet Friendly!
Don't see what you're looking for?
See all available properties in Chesterfield
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.

Other property types in Chesterfield

Charming Waterfront Log Cabin
Property grounds
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, (27)
"This cabin is so wonderful. The linens are exquisite and the beds are super comfortable. It is decorated so cute. There is everything you need! My favorite activity was sitting in the wooden rocking chair on the front porch each morning, drinking coffee, listening to nature (frogs, fish), and watching the lovely pond (which is so big it should be called a lake!) The owner responded to all my questions within minutes. You can even have pizza (regular AND gluten free) delivered!! If you visit, you...
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
9.0 out of 10, Wonderful, (25)
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Rear Deck for barbecues looking across rear yard.
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (9)
"The grounds were well kept. The house was remodeled and very clean. Lots of room. Equipped with everything you would need. Quiet. Owners were awesome to deal with and easy to get ahold of. I would definitely recommend people to stay there. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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, April, and November, 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.

Recent reviews of Chesterfield hotels
Expedia verified reviews

Colonial Motel And Spa

Colonial Motel And Spa

5/5 Excellent
"Great spot"
A verified traveler stayed at Colonial Motel And Spa
Posted 22 hours ago
Colonial Motel And Spa