Find Romantic Hotels in Chesterfield, MA from $104

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Check availability on Chesterfield Romantic Hotels

Our top choices for Chesterfield romantic hotels

Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2246)
"Stayed 3 nights, really great hotel and value. "
United States
Vince
$121 nightly
The price is $135
Dec 15 - Dec 16
Total with taxes and fees
D. Hotel Suites & Spa
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (985)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$93 nightly
The price is $104
Dec 15 - Dec 16
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property - evening/night
Inn on Boltwood

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (749)
"Room was clean and the bed was very comfortable. "
United States
Michael
$199 nightly
The price is $222
Dec 14 - Dec 15
Total with taxes and fees
Inn on Boltwood
Front of property
Hotel Northampton

Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1000)
"Beautiful historic property with great dining options."
United States
Mark
$165 nightly
The price is $184
Dec 14 - Dec 15
Total with taxes and fees
Hotel Northampton
Terrace/patio
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (269)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
$187 nightly
The price is $209
Dec 13 - Dec 14
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
Exterior
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
$149 nightly
The price is $157
Dec 13 - Dec 14
Total with taxes and fees
UU Rowe Camp and Conference Center
Property amenity
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (682)
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
$143 nightly
The price is $160
Dec 21 - Dec 22
Total with taxes and fees
Courtyard by Marriott Hadley Amherst
Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
$200 nightly
The price is $212
Jan 7 - Jan 8, 2026
Total with taxes and fees
Harbour House Inn
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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Top Chesterfield Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Stayed 3 nights, really great hotel and value. "
Vince 3-night trip
Posted 1 day ago
D. Hotel Suites & Spa

Frequently asked questions

Searching for romantic hotels in Chesterfield?
If you and your partner need a romantic vacation, we've got just the thing. If you want to explore the area, you might head to Chesterfield Gorge, Chesterfield Gorge Reservation, or Westfield River. If you're interested in staying close to a certain attraction, you can sort by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chesterfield?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chesterfield: The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chesterfield?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Chesterfield has to offer. A visit to Chesterfield Gorge, Chesterfield Gorge Reservation, or Westfield River might be just the ticket when you're checking out the sights.
What's the best way to get to Chesterfield and around town during my romantic getaway?
These transportation options in Chesterfield might help your romantic trip get off to a smooth start: The closest major airport is Westfield, MA (BAF-Barnes Municipal), located 16.6 mi (26.8 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.

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