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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

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
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

The price is SAR 281
SAR 725 total
includes taxes & fees
27 Mar - 28 Mar
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, (14)
"Great experience. "
Updated Vintage Apartment < 1/2 Mi to Main St
Lake Whitingham & Mount Snow Area Village Apartment
Outdoor dining

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 1,143 total
includes taxes & fees
27 Mar - 28 Mar
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
Outdoor dining

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!
Outdoor dining

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (13)
"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!
Fridge, microwave, oven, stovetop

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (129)
"A terrific, cozy place, convenient, in a cute neighborhood -- super easy check in --- clear directions --- couldn't ask for anything more."
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.

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 detail

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
Down Under the Hall House
Interior

Down Under the Hall House

The price is SAR 360
SAR 492 total
includes taxes & fees
27 Mar - 28 Mar
Down Under the Hall House
'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
Property grounds

Spacious 4-bedroom apartment in awesome Guilford with AC

The price is SAR 2,107
SAR 2,793 total
includes taxes & fees
1 Apr - 2 Apr
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

The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"The Jelly Mill is a lovely, welcoming cottage in the S. VT town of Guilford, nestled in the hills below the bigger town of Brattleboro. The location feels 'out of the way' - no big roads (or even paved roads), stores, 'hustle or bustle' anywhere close by - but Brattleboro has all that stuff and is only 20-30 minutes away. For 'last minute' items a charming, smaller grocery / sandwich shop is closer by. The property itself is very clean, with an up to date kitchen and glitch-free speedy Wi-Fi...
The Jelly Mill-A River Retreat
Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is SAR 1,125
SAR 1,966 total
includes taxes & fees
14 Apr - 15 Apr
Cozy Home Near Downtown, Shops, and Restaurants.
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (35)
"We were more than impressed by this property, and surpised by the total freedom from other people on the lands. We loved staying at this charming property that is rustic and thoughtfully decorated. The views are amazing and the place is completely quiet. There is a long driveway up from the 'main road', which is really a very lightly traveled road anyway. We enjoyed the silence, and the bucolic views and lifestyle. It was late winter and there was snow on the ground when we arrived, but the...
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
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 top apartments in the area to choose from: Beautiful Townhouse In Turners Falls!: Located 20.1 mi/32.3 km away in Montague. Laundry facilities and private balconies are included. Lake Whitingham & Mount Snow Area Village Apartment: It’s situated in Jacksonville, 18.9 mi/30.4 km away. Includes free WiFi and Smart TVs. Lakefront Orange Vacation Rental - Pet Friendly!: 21 mi/33.8 km away in Orange. Amenities include fireplaces. The Covey House Retreat with InfraRed Sauna: Located in Fitzwilliam, 18.1 mi/29.1 km from Chesterfield. Includes free WiFi and Smart TVs. 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 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.