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Recommended hotels in Chesterfield

Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
$238 nightly
The price is $294
Jun 3 - Jun 4
Total with taxes and fees
Deerfield Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
"It was a clean, friendly hotel."
United States
Cheri
$113 nightly
The price is $126
Jun 4 - Jun 5
Total with taxes and fees
Quality Inn Lee - Lenox South

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
$114 nightly
The price is $127
Jun 7 - Jun 8
Total with taxes and fees
Berkshire Lake Lodge

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,194 reviews)
"Spacious room, very helpful staff, good coffee and an excellent breakfast."
United States
Clifford
$111 nightly
The price is $124
Jun 14 - Jun 15
Total with taxes and fees
D. Hotel Suites & Spa

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (960 reviews)
"Great location and resort. Very happy with accommodation's"
United States
Robert
$155 nightly
The price is $173
Jun 2 - Jun 3
Total with taxes and fees
Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (99 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
$132 nightly
The price is $147
Jun 7 - Jun 8
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (136 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
$144 nightly
The price is $155
Jun 2 - Jun 3
Total with taxes and fees
Blooming Inn

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (162 reviews)
"Friendly staff, great under the radar spot alternative to chain motels!"
United States
Anthony
$116 nightly
The price is $130
Jun 22 - Jun 23
Total with taxes and fees
River Valley Inn

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,000 reviews)
"Clean room, great staff, parking"
United States
Gail
$99 nightly
The price is $110
Jul 1 - Jul 2
Total with taxes and fees
Red Roof Inn PLUS+ South Deerfield – Amherst

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (124 reviews)
"My wife and I had a wonderful stay for a long weekend. The breakfast was delicious and the staff were kind and friendly."
United States
Andrew
$185 nightly
The price is $207
Jul 1 - Jul 2
Total with taxes and fees
Black Walnut Inn

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,006 reviews)
"Lovely location and very helpful staff."
United States
Daniel
$130 nightly
The price is $145
Jun 28 - Jun 29
Total with taxes and fees
Hotel UMass

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,002 reviews)
"Our room was very clean, staff was very friendly. We would stay here again."
United States
Sherry
$89 nightly
The price is $101
Jun 21 - Jun 22
Total with taxes and fees
Hampton Inn West Springfield

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (32 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
$166 nightly
The price is $185
Jun 16 - Jun 17
Total with taxes and fees
The Revival House

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (861 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
$122 nightly
The price is $136
Jun 28 - Jun 29
Total with taxes and fees
Hampton Inn Westfield

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (934 reviews)
"Very clean& maintained. Most comfortable bed I've slept in"
United States
Keith
$101 nightly
The price is $113
Jun 29 - Jun 30
Total with taxes and fees
Quality Inn Westfield - Springfield

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"Beautifully appointed and comfortable. "
United States
Emily Kate G.
$180 nightly
The price is $201
Jun 8 - Jun 9
Total with taxes and fees
Lovely 2nd Floor Apartment

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (88 reviews)
"Friendly staff, clean room, awesome breakfast"
United States
Matthew
$180 nightly
The price is $201
Jun 14 - Jun 15
Total with taxes and fees
TownePlace Suites by Marriott Hadley Amherst

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (243 reviews)
"Had a great stay."
United States
Trevor
$77 nightly
The price is $85
Jun 8 - Jun 9
Total with taxes and fees
Rodeway Inn

Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (52 reviews)
"Daniel Stebbins House was wonderful. Beautiful rooms. Next to downtown. Enjoyable breakfast. Fabulous experience!"
United States
Holly
$270 nightly
The price is $302
Jun 3 - Jun 4
Total with taxes and fees
Daniel Stebbins House

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,004 reviews)
"It was a great stay."
United States
Geovani
$115 nightly
The price is $130
Jun 22 - Jun 23
Total with taxes and fees
Tru by Hilton Chicopee Springfield
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

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
10,676
Accommodation
53 Cottages
Lowest Price
$81
Highest Price
$294

Frequently asked questions

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How can I find cheap cottages in Chesterfield?
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What is there to do in Chesterfield near my cottage?
The best travel accessory is a well-planned to-do list. Chesterfield Gorge is a great place to begin your exploration of Chesterfield.

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