Chesterfield Winter Rentals & Holiday Homes

Discover winter rentals Chesterfield - We found 24 exact matches

About Chesterfield Winter Rental on Online Reservations

At Online Reservations, we feature a wide range of listings for accommodations in Chesterfield, MA that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. Online Reservations winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you are escaping the snow or running to it, Online Reservations helps connect you to the best cabins, bungalows, lodges, and rent-by-owner homes, as well as the best places to stay in both sun and ski resorts. Online Reservations will make your winter getaway an unforgettable experience.

Online Reservations offers luxury finds for travelers planning on renting a place in Chesterfield, to enjoy these benefits and to book your winter vacation homes, go to the Online Reservations filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Chesterfield and unlock even more amazing deals.Plan Your Perfect Escape with Online Reservations.

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Frequently Asked Questions About Chesterfield Winter Rentals

There are a lot of options in Chesterfield. If you plan on staying in the Chesterfield area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Chesterfield:

The average cost for winter rentals in Chesterfield is $484 per night. Online Reservations has a wide list of great winter places to stay near Chesterfield that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Chesterfield that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Chesterfield on Online Reservations

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Chesterfield to find what works for you.
As of 2025, the data from Online Reservations shows that there are over 24 private swimming pools or indoor pools accommodations near Chesterfield along with other great amenities.

About 24 holiday rentals in Chesterfield boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Chesterfield for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Chesterfield with all the best amenities for your next trip.