Search Resort Hotels in Chesterfield from CA $99

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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, (1,008 reviews)
"great and quaint stay"
United States
Adalie
The price is CA $142
CA $158 total
includes taxes & fees
Dec 7 - Dec 8
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
The price is CA $119
CA $133 total
includes taxes & fees
Nov 22 - Nov 23
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
The price is CA $125
CA $140 total
includes taxes & fees
Dec 6 - Dec 7
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, (1,001 reviews)
"Lovely room, great location, staff excellent"
United States
Lyla
The price is CA $134
CA $151 total
includes taxes & fees
Nov 9 - Nov 10
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
The price is CA $170
CA $190 total
includes taxes & fees
Nov 17 - Nov 18
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, (1,001 reviews)
"nice place to stay in the heart of downtown Northampton"
United States
Beth
The price is CA $208
CA $233 total
includes taxes & fees
Nov 12 - Nov 13
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
The price is CA $100
CA $180 total
includes taxes & fees
Nov 8 - Nov 9
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, (1,001 reviews)
"Very clean spacious room and friendly staff. Will definitely stay here again!!"
United States
Jennifer
The price is CA $167
CA $186 total
includes taxes & fees
Dec 1 - Dec 2
Comfort Inn & Suites Hadley - Amherst
A modern kitchen with a central island, a refrigerator, and a coffee station.

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
The price is CA $166
CA $185 total
includes taxes & fees
Nov 30 - Dec 1
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
The price is CA $206
CA $230 total
includes taxes & fees
Nov 16 - Nov 17
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
The price is CA $211
CA $236 total
includes taxes & fees
Nov 9 - Nov 10
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, (1,001 reviews)
"Perfect for a travel stop-over."
United States
James
The price is CA $119
CA $133 total
includes taxes & fees
Dec 2 - Dec 3
Quality Inn Lee - Lenox South
A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

13. D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,090 reviews)
"Very comfortable beds nice clean bathroom Excellent hot breakfast"
United States
Luke
The price is CA $165
CA $193 total
includes taxes & fees
Nov 29 - Nov 30
D. Hotel Suites & Spa
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

14. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is CA $163
CA $182 total
includes taxes & fees
Nov 29 - Nov 30
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
The price is CA $247
CA $276 total
includes taxes & fees
Nov 15 - Nov 16
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
The price is CA $144
CA $161 total
includes taxes & fees
Dec 6 - Dec 7
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
The price is CA $201
CA $225 total
includes taxes & fees
Nov 29 - Nov 30
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
The price is CA $257
CA $339 total
includes taxes & fees
Nov 29 - Nov 30
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, (403 reviews)
"Overall great stay! Very helpful staff and the rooms were beautiful. I stayed alone and felt very comfortable."
United States
Samantha
The price is CA $142
CA $162 total
includes taxes & fees
Nov 30 - Dec 1
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
The price is CA $206
CA $230 total
includes taxes & fees
Nov 29 - Nov 30
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.
View all properties

Top reviews in Chesterfield

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

The Ellery

The Ellery
Northampton

10/10 Excellent

We stayed 5 days in the ground floor coach house room which was a lovely, large room with a sitting and dinning area as well as a private patio area. The room was lovely, AC worked great on an extremely hot week and the breakfast, all days snacks and common area were great as well. The staff was helpful with tips about things to do in the area. We had a great visit.
Canada
Graham
Reviewed July 5, 2026
The Ellery

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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