Search Vacation Homes in Chesterfield
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Chesterfield vacation homes
Vacation Home in Greenfield
Lovely 2nd Floor Apartment10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
Wendy M.
$180 nightly
The price is $201
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Keene
Downtown Hot Tub Escape9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
Jack P.
$256 nightly
The price is $277
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Colrain
Couples 2 Bedroom Retreat-Close to Shelburne Falls10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
KayKay S.
$316 nightly
The price is $352
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Putney
Family Friendly Hilltop House In Putney Vermont9.4 out of 10, Exceptional, (57)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
Louis T.
$236 nightly
The price is $265
Dec 15 - Dec 16
Total with taxes and fees
Vacation Home in Guilford
Stunning Glass House nestled in the Vermont wilderness!10.0 out of 10, Exceptional, (1)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
Grant D.
$369 nightly
The price is $413
Dec 16 - Dec 17
Total with taxes and fees
Vacation Home in Walpole
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 910.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
mary c.
$513 nightly
The price is $557
Dec 16 - Dec 17
Total with taxes and fees
Vacation Home in Colrain
FaLL Western Mass Getaway-Airhockey-Firepit9.8 out of 10, Exceptional, (38)
"Great house for family gatherings "
John Paul B.
$591 nightly
The price is $660
Dec 12 - Dec 13
Total with taxes and fees
Vacation Home in Whitingham
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed10.0 out of 10, Exceptional, (14)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
Jacklyn D.
$527 nightly
The price is $590
Dec 14 - Dec 15
Total with taxes and fees
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.
Find vacation rentals that suit your style
Cabins
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Chesterfield Hotel Reviews
Latchis Hotel
10/10 Excellent
Find out more about Chesterfield
Chesterfield Vacation Homes information
Number of reviews | 224 |
|---|---|
Accommodation | 149 Vacation Homes |
Lowest Price | $201 |
Highest Price | $674 |
Explore a world of travel with Expedia
- Hotels near Asbury United Methodist Church
- B&B in West Chesterfield
- Cabin Rentals in West Chesterfield
- Motels in West Chesterfield
- Resorts in West Chesterfield
- Hotels near Spofford Lake
- West Chesterfield Hotels
- Resorts & Hotels with Spas in West Chesterfield
- Hotel Wedding Venues Hotels in West Chesterfield
- Hotels on the River in West Chesterfield
- Golf Hotels in West Chesterfield
- Historic Hotels in West Chesterfield
- 4 Star Hotels in West Chesterfield
- Pet-friendly Hotels in West Chesterfield
- Hotels near Actors Theatre Playhouse
- Hotels near Madame Sherri Forest
- Hotels near Madame Sherris Castle Ruins
- Cottages in Spofford
- B&B in Spofford
- Motels in Spofford
- Cabin Rentals in Spofford
- Apartments in Spofford
- Lodges in Spofford
- Vacation Homes in Spofford
- Spofford Hotels
- 3 Star Hotels in Spofford
- Hotels near Chesterfield Gorge Natural Area
- Hotels near Wantastiquet Mountain
- Hotels near United States Navy Seabee Bridge
- Cabin Rentals in Westmoreland
- Chalets in Westmoreland
- B&B in Westmoreland
- Motels in Westmoreland
- Apartments in Westmoreland
- Vacation Homes in Westmoreland
- Cottages in Westmoreland
- Westmoreland Hotels
- 4 Star Hotels in Westmoreland
- Cottages in Hinsdale
- B&B in Hinsdale
- Motels in Hinsdale
- Hinsdale Hotels
- Hotels near Stonewall Farm
- 4 Star Hotels in Hinsdale
- 5 Star Hotels in Hinsdale
- 3 Star Hotels in Hinsdale
- Vacation Homes in Ashuelot
- Ashuelot Hotels
- Hotels near Alumni Field
- B&B in Winchester
- Cottages in Winchester
- RV Parks in Winchester
- Apartments in Winchester
- Guest Houses in Winchester
- Vacation Homes in Winchester
- Cabin Rentals in Winchester
- Winchester Hotels
- Historic Hotels in Winchester
- Vacation Homes in Swanzey
- B&B in Swanzey
- Motels in Swanzey
- Cabin Rentals in Swanzey
- Cottages in Swanzey
- Keene Hotels
- Swanzey Hotels
- Hotels near Ashuelot River
- Pet-friendly Hotels in Swanzey
- 4 Star Hotels in Swanzey
- Romantic Hotels in Swanzey