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Best Resorts in Chesterfield

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterfield

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

1. The Ellery

The Ellery
3.5 star property
Northampton
9.4 out of 10, Exceptional, (1,006 reviews)
"great and quaint stay"
United States
Adalie
$104 nightly
The price is $116
Dec 2 - Dec 3
Total with taxes and fees
The Ellery
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

2. River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (305 reviews)
"Super friendly and helpful staff, convenient parking, decently sized room."
United States
Brandon
$82 nightly
The price is $92
Dec 6 - Dec 7
Total with taxes and fees
River Valley Inn
A hotel reception area with a stone wall, leather chairs, a reception desk, and a sign indicating free Wi-Fi.

3. 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, (1,007 reviews)
"Room was neat and clean, air conditioning worked great and helped keep the room at a cool temperature. Friendly staff, easy location, a would recommend for a quick stay."
United States
Jack
$89 nightly
The price is $100
Dec 6 - Dec 7
Total with taxes and fees
Red Roof Inn PLUS+ South Deerfield – Amherst
A modern living room with a fireplace, red curtains, and a wooden dining table.

4. Hotel UMass

Hotel UMass
2.5 star property
Amherst
9.0 out of 10, Wonderful, (1,000 reviews)
"Lovely room, great location, staff excellent"
United States
Lyla
$88 nightly
The price is $98
Dec 6 - Dec 7
Total with taxes and fees
Hotel UMass
A hotel lobby with a bar area, dining tables, and comfortable seating.

5. Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (1,001 reviews)
"SPacious room, indoor pool, easy drive to Northampton. We enjoyed our stay."
United States
Esther
$121 nightly
The price is $135
Nov 17 - Nov 18
Total with taxes and fees
Hampton Inn Hadley-Amherst Area
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.

6. Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,000 reviews)
"nice place to stay in the heart of downtown Northampton"
United States
Beth
$165 nightly
The price is $184
Nov 12 - Nov 13
Total with taxes and fees
Hotel Northampton
A two-story house with a porch, a balcony, and a chimney.

7. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
United States
Robert
$129 nightly
The price is $138
Nov 8 - Nov 9
Total with taxes and fees
Blooming Inn
A hotel with a covered entrance, a flag, and a clear sky.

8. Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,000 reviews)
"Very clean spacious room and friendly staff. Will definitely stay here again!!"
United States
Jennifer
$119 nightly
The price is $133
Dec 1 - Dec 2
Total with taxes and fees
Comfort Inn & Suites Hadley - Amherst
A modern restaurant with high tables and bar stools, a fireplace, and a TV mounted on the wall.

9. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
2.5 star property
Northampton
7.2 out of 10, Good, (1,001 reviews)
"The hotel is a great place to stay for a trip in this area."
United States
Ni-Ling
$118 nightly
The price is $132
Nov 30 - Dec 1
Total with taxes and fees
Quality Inn & Suites Northampton - Amherst
A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.

10. Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
3.0 star property
Northampton
9.2 out of 10, Wonderful, (1,006 reviews)
"Nice, clean, room; friendly staff; good breakfast options"
United States
Erik
$147 nightly
The price is $164
Nov 16 - Nov 17
Total with taxes and fees
Fairfield Inn & Suites Springfield Northampton/Amherst
A view of a red building by a waterway through a window.

11. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (552 reviews)
"The Old Mill is a great, unique hotel for staying in Western MA. The room was well decorated to match the historic usage of the building. Also, the bed was comfortable and the bathroom was great. It’s very convenient for getting around by I91 and 5&10. The area is beautiful in the fall."
United States
Wayne
$149 nightly
The price is $166
Nov 16 - Nov 17
Total with taxes and fees
Old Mill Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

12. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect for a travel stop-over."
United States
James
$85 nightly
The price is $95
Dec 2 - Dec 3
Total with taxes and fees
Quality Inn Lee - Lenox South
An outdoor patio with white chairs and tables, a central fire feature, and string lights.

13. D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,089 reviews)
"Very comfortable beds nice clean bathroom Excellent hot breakfast"
United States
Luke
$117 nightly
The price is $130
Dec 6 - Dec 7
Total with taxes and fees
D. Hotel Suites & Spa
A building entrance with a large planter with purple flowers and a small tree.

14. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (979 reviews)
"Very nice hotel"
United States
Philip
$119 nightly
The price is $133
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North
An indoor swimming pool with clear water, surrounded by windows with a view of trees.

15. Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (978 reviews)
"Staff were excellent!!! THANK YOU!"
United States
Quentin
$135 nightly
The price is $151
Dec 6 - Dec 7
Total with taxes and fees
Hampton Inn & Suites Greenfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.

16. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
$103 nightly
The price is $115
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
An outdoor patio area with a circular fire pit surrounded by wicker chairs and tables.

17. TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (113 reviews)
"What a lovely property- such a great place to stay when in the Amherst area - staff is excellent- the rooms are all perfect and the amenities are outstanding"
United States
Sarah
$144 nightly
The price is $160
Nov 29 - Nov 30
Total with taxes and fees
TownePlace Suites by Marriott Hadley Amherst
A historic building with a covered porch, American flags, and a sign reading 'Deerfield Inn.'

18. Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
9.8 out of 10, Exceptional, (40 reviews)
"Excellent stay!"
United States
Debbie
$169 nightly
The price is $208
Dec 1 - Dec 2
Total with taxes and fees
Deerfield Inn
A modern lounge area with sofas, a pool table, and a unique chandelier.

19. Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel
2.0 star property
West Springfield
9.2 out of 10, Wonderful, (400 reviews)
"Overall great stay! Very helpful staff and the rooms were beautiful. I stayed alone and felt very comfortable."
United States
Samantha
$101 nightly
The price is $116
Nov 26 - Nov 27
Total with taxes and fees
Blue A Modern Hotel, an Ascend Collection Hotel
A modern hotel lobby with a stone wall, a fireplace, a bar area, and seating arrangements.

20. Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (848 reviews)
"Great breakfast, excellent staff"
United States
Jenny
$147 nightly
The price is $164
Nov 17 - Nov 18
Total with taxes and fees
Homewood Suites by Hilton Hadley Amherst
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

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Was a great stay, very clean, quiet, and breakfast was good."
Jose 2-night trip
Posted less than an hour ago
Tru by Hilton Chicopee Springfield

Find out more about Chesterfield

Chesterfield Resorts information

Number of reviews
7,262
Accommodation
0 Resorts
Lowest Price
$92
Highest Price
$208

Frequently asked questions

What can I expect from a resort vacation in Chesterfield?
You deserve a getaway, and a resort is just the place to pamper yourself with the amenities and services you need for a relaxing time in Chesterfield. One of the comfortable resorts in the surrounding area might be just what you're looking for, whether you want an amazing pool, a state-of-the-art fitness center, or nightly entertainment options.
What's the best resort in Chesterfield?
Our top-rated resort near Chesterfield: Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! - 21.7 mi (34.9 km) from Chesterfield. Features a fitness center, an indoor pool, and an outdoor pool.
What can I do in Chesterfield?
Chesterfield Gorge, Chesterfield Public Library, and Chesterfield Town Hall are a few of the interesting sights to visit. Chesterfield Gorge Reservation and Silvio O. Conte National Fish and Wildlife Refuge are a few additional attractions in the area that you might like.
What's the weather like 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's the best way to get to and around Chesterfield?
Fly into Westfield, MA (BAF-Barnes Municipal), which is located 16.6 mi (26.8 km) from the heart of the city. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.2 mi (37.3 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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