Chesterfield Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Chesterfield hotels

Cottages in Chesterfield

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington VT

With a stay at this cottage in Wilmington, you'll be near the beach, just a 1-minute walk from Lake Raponda and 12 minutes by foot from The Art of Humor Gallery.

Waterfront Cottage on Scenic Sportsman Pond

Fitzwilliam NH

With a stay at this cottage in Fitzwilliam, you'll be on the waterfront, just steps from Sportsman Pond and a 4-minute drive from Lawrence Brook WMA.

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole NH

$231 nightly

$250 total

Mar 8 - Mar 9

Total with taxes and fees

Located in Walpole, this cottage is in a rural location, within a 10-minute drive of Connecticut River and Walpole Artisans Cooperative.

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington VT

With a stay at this cottage in Wilmington, you'll be within a 10-minute drive of Mount Snow and North Branch Deerfield River.

10 Mi to Mt Snow! Grand Estate Built to Entertain

Wilmington VT

With a stay at this cottage in Wilmington, you'll be steps from The Art of Humor Gallery and a 3-minute drive from Lake Raponda.

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

Newfane VT

Located in Newfane, this cottage is in a rural location, a 3-minute drive from Rock River Preserve and 7 minutes from West River.

Charming Putney Home: Porch, Grill & Hiking Trails

Putney VT

Located in Putney, this cottage is a 4-minute drive from The Putney School and 6 minutes from Hidden Springs Maple.

Hiking Trails On-site: Cozy Falls Brook Cabin

Brattleboro VT

When you stay at this cottage in Brattleboro, you'll be within a 10-minute drive of West River and Rock River Preserve.

Charming Jaffrey Cottage w/ Deck & Grill!

Jaffrey NH

With a stay at this cottage in Jaffrey, you'll be steps from Shattuck Golf Course and a 2-minute drive from Monadnock Reservation.

Recently Renovated Cozy Cottage in Private Village On VT-100 (5-min to Mount Snow)

West Dover VT

With a stay at this cottage in West Dover, you'll be within a 10-minute drive of Mount Snow and Green Mountain National Forest.

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

Vernon VT

With a stay at this cottage in Vernon, you'll be steps from Norcross Wildlife Sanctuary and a 2-minute drive from Satan's Kingdom Wildlife Management Area.

Historic Home w/ Modern Updates on < 4 Acres

Royalston MA

With a stay at this cottage in Royalston, you'll be within a 5-minute drive of Royalston State Forest and Royalston Falls.

Don't see what you're looking for?

See all available properties in Chesterfield

View all properties

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.