Vacation Homes in Chesterfield, MA
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Top Vacation Homes in Chesterfield

Peace and quiet on the lake

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Cozy 1-bedroom house in overlooking the river close to downtown Northampton

19th c. Barn in the Berkshires

Lovely 2nd Floor Apartment

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Becket Home w/ 3-Season Porch: Walk to Lake Access

Historic Farmhouse Near Mountains & Colleges!

Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge

Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Top hotels in Chesterfield

D. Hotel Suites & Spa
Find the Best Vacation Homes in Chesterfield
Why book a vacation home in Chesterfield?
Vacation homes in Chesterfield make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Chesterfield?
Private Chesterfield rental homes range between $106 - $201 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Chesterfield vacation home rentals. You might look for Chesterfield rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Chesterfield offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Chesterfield?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chesterfield. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chesterfield hotels and vacation homes that best suit your stay. We also have deals for flights, and Chesterfield car rentals. You’ll save even more when you bundle your items into a Chesterfield vacation package!
How many vacation homes are available to book in Chesterfield?
There are 161 rental homes in Chesterfield. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Chesterfield?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Chesterfield Vacation Homes essential information
Accommodation | 161 Vacation Homes |
|---|---|
Lowest Price | $106 |
Highest Price | $201 |
Popular accommodation | Peace and quiet on the lake, kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley, Cozy 1-bedroom house in overlooking the river close to downtown Northampton, 19th c. Barn in the Berkshires, Lovely 2nd Floor Apartment, Hawley Home w/ Deck: 4 Mi to Berkshire East Resort, Becket Home w/ 3-Season Porch: Walk to Lake Access, Historic Farmhouse Near Mountains & Colleges!, Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge, Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village., Old World Charm, Modern Conveniences - 3 BR private home in quiet setting, The Meadows House @ Otis Ridge w/ 7-person hot tub |






