Default HTG hotel image

Chesterfield Hotels from S$89

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Filter by

Star rating

Guest rating

Our top choices for Chesterfield hotels

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
A hotel room with a bed, a sofa, a dining table, and a chair. There are two nightstands with lamps and a framed picture on the wall.
A modern hotel room with a dining area, a sofa, a bed, and a TV.
A brick building with a sign reading "The Ellery."

1. The Ellery

The Ellery
Northampton
United States
Travis
S$181
includes taxes & fees
28 Oct - 29 Oct
The Ellery
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
A hotel room with two beds, a TV, a desk, and a chair.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.

2. Hotel Northampton

Hotel Northampton
Northampton
United States
Beth
S$212
includes taxes & fees
27 Oct - 28 Oct
Hotel Northampton
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.
A bathroom with a bathtub, toilet, and shower curtain.
A row of single-story motel buildings with a parking lot in front.
A bathroom with a toilet, a shower, and a towel rack.

3. River Valley Inn

River Valley Inn
West Hatfield
United States
Michael
S$120
includes taxes & fees
1 Nov - 2 Nov
River Valley Inn
A hotel lobby with a bar area, dining tables, and comfortable seating.
A lobby with two armchairs, a fireplace, and a framed picture on the wall.
A large, multi-story hotel with a covered entrance and a parking lot.
A deck with a table and chairs, a large umbrella, and a view of a lawn and trees.

4. Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
Hadley
S$191
includes taxes & fees
29 Oct - 30 Oct
Hampton Inn Hadley-Amherst Area
A gaming area with arcade machines, a seating area with tables and chairs, and large windows providing natural light.
A Red Roof Plus hotel with a modern facade, a parking lot, and a landscaped entrance area.
A hotel room with a television displaying a football game, a desk with a lamp, a microwave, and a refrigerator.
A hotel room with two beds, a desk, a chair, a TV, and a mirror.

5. Red Roof Inn PLUS+ South Deerfield โ€“ Amherst

Red Roof Inn PLUS+ South Deerfield โ€“ Amherst
South Deerfield
United States
Edward
S$128
includes taxes & fees
1 Nov - 2 Nov
Red Roof Inn PLUS+ South Deerfield โ€“ Amherst
A swimming pool area with a hot tub, a no diving sign, and a chair near the pool.
An indoor swimming pool with clear signage, a lifeguard chair, and a no diving warning.
Room
A multi-story hotel with a parking lot in front.

6. Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
Hadley
United States
John
S$169
includes taxes & fees
4 Nov - 5 Nov
Comfort Inn & Suites Hadley - Amherst
A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.
A modern hotel dining area with multiple tables and chairs, pendant lighting, and a view of the city through large windows.
An indoor swimming pool with clear glass walls, a poolside seating area, and a reception desk.
A Fairfield by Marriott hotel with a modern entrance, American flags, and a stone facade.

7. Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
Northampton
United States
Nancy
S$206
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites Springfield Northampton/Amherst
An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.
A spacious lobby with a central seating area, a reception desk, and a television screen.
A hotel room with two beds, a desk with a chair, a TV, and a large window with curtains.
A dining table set with multiple wine glasses, a centerpiece with flowers, and candles.

8. Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
Hadley
United States
Yuki
S$205
includes taxes & fees
28 Oct - 29 Oct
Courtyard by Marriott Hadley Amherst
A view of a red building by a waterway through a window.
A yellow multi-story building with a water feature in front.
A wooden porch with a sign reading "OLD MILL" above a double door.
A bar area with wooden stools, a long counter, and potted plants.

9. Old Mill Inn

Old Mill Inn
Hatfield
United States
John
S$257
includes taxes & fees
3 Nov - 4 Nov
Old Mill Inn
A two-story house with a porch, a balcony, and a chimney.
A dining room with a wooden table, chairs, a chandelier, and a fireplace.
A traditional dining room with a wooden table, chairs, and a chandelier.
A traditional living room with a green sofa, a yellow armchair, a wooden coffee table, and a patterned rug.

10. Blooming Inn

Blooming Inn
Shelburne Falls
United States
Robert
S$161
includes taxes & fees
4 Nov - 5 Nov
Blooming Inn
A modern restaurant with high tables and bar stools, a fireplace, and a TV mounted on the wall.
A hotel lobby with a reception desk, seating area, and a large aquarium.
A vending machine stocked with snacks and beverages, and shelves with packaged goods.
A room with a grey sofa, a small table, a lamp, a door, and a framed abstract artwork on the wall.

11. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
Northampton
United Kingdom
Glenn
S$175
includes taxes & fees
9 Nov - 10 Nov
Quality Inn & Suites Northampton - Amherst
An outdoor patio with white chairs and tables, a central fire feature, and string lights.
A hotel with a sign reading "D. HOTEL & SUITES" on the facade.
A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.
A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

12. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Jim
S$182
includes taxes & fees
26 Oct - 27 Oct
D. Hotel Suites & Spa
An outdoor patio area with a circular fire pit surrounded by wicker chairs and tables.
A modern hotel with a covered entrance, outdoor seating, and a brick facade.
A modern kitchen with a built-in microwave, stainless steel refrigerator, and a wooden cabinet above the sink.
An indoor swimming pool with clear safety signage, a sunlit area with seating, and a view through large windows.

13. TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
Hadley
United States
Sarah
S$225
includes taxes & fees
8 Nov - 9 Nov
TownePlace Suites by Marriott Hadley Amherst
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.

14. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
S$133
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Lee - Lenox South
A modern living room with a fireplace, red curtains, and a wooden dining table.
A hotel room with two beds, a dining table with a plate of food, a glass of water, and a bottle of wine.
A modern building with a grid-like facade, multiple balconies, and a spacious courtyard with geometric sculptures.
A registration desk with a sign above it, a receptionist, and several people standing in line.

15. Hotel UMass

Hotel UMass
Amherst
United States
Darrell
S$159
includes taxes & fees
9 Nov - 10 Nov
Hotel UMass
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A snack bar with shelves of snacks and a refrigerated display.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ginger
S$142
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A breakfast area with a waffle station, coffee machine, and various food options.
A modern hotel room with a flat-screen TV on a wooden desk, a blue office chair, and a large window with abstract art.
A fitness room with treadmills, an elliptical, and a stationary bike.
A modern hotel room with a large bed, a desk, and a chair.

17. Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
Chicopee
United States
Gary
S$159
includes taxes & fees
1 Nov - 2 Nov
Tru by Hilton Chicopee Springfield
A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.
A hotel lobby with a seating area, a bar, and a TV screen.
A spacious lobby with a reception desk, a blue decorative wall, and a wooden floor.
A hotel lobby with a reception desk, seating area, and large windows.

18. Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
Holyoke
United States
Caroline
S$181
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites Springfield Holyoke
A hotel reception area with a wooden reception desk, two pendant lights, a minibar, and a refrigerator stocked with beverages.
A modern hotel with a brick facade, multiple windows, and a well-lit entrance.
An outdoor seating area with chairs and tables, a covered patio with string lights, and potted plants.
A modern hotel lobby with a stone wall, a fireplace, a bar area, and seating arrangements.

19. Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
Hadley
United States
Rebecca
S$222
includes taxes & fees
1 Nov - 2 Nov
Homewood Suites by Hilton Hadley Amherst
A modern lounge area with sofas, a pool table, and a unique chandelier.
A modern hotel lobby with blue sofas, a bar area, and a decorative chandelier.
A modern hotel with a covered entrance, multiple windows, and a well-maintained lawn.
A modern coffee bar with espresso machines, a coffee station, and a shelf with coffee products.

20. Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel
West Springfield
United States
Charles
S$157
includes taxes & fees
25 Oct - 26 Oct
Blue A Modern Hotel, an Ascend Collection Hotel
View all properties

Hotels recommended for families in Chesterfield

A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.
A modern hotel dining area with multiple tables and chairs, pendant lighting, and a view of the city through large windows.
An indoor swimming pool with clear glass walls, a poolside seating area, and a reception desk.
A Fairfield by Marriott hotel with a modern entrance, American flags, and a stone facade.

Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
Northampton
S$206
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites Springfield Northampton/Amherst
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
A hotel room with two beds, a TV, a desk, and a chair.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.

Hotel Northampton

Hotel Northampton
Northampton
S$212
includes taxes & fees
27 Oct - 28 Oct
Hotel Northampton
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
A hotel room with a bed, a sofa, a dining table, and a chair. There are two nightstands with lamps and a framed picture on the wall.
A modern hotel room with a dining area, a sofa, a bed, and a TV.
A brick building with a sign reading "The Ellery."

The Ellery

The Ellery
Northampton
S$181
includes taxes & fees
28 Oct - 29 Oct
The Ellery
A swimming pool area with a hot tub, a no diving sign, and a chair near the pool.
An indoor swimming pool with clear signage, a lifeguard chair, and a no diving warning.
Room
A multi-story hotel with a parking lot in front.

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
Hadley
S$169
includes taxes & fees
4 Nov - 5 Nov
Comfort Inn & Suites Hadley - Amherst
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.
A bathroom with a bathtub, toilet, and shower curtain.
A row of single-story motel buildings with a parking lot in front.
A bathroom with a toilet, a shower, and a towel rack.

River Valley Inn

River Valley Inn
West Hatfield
S$120
includes taxes & fees
1 Nov - 2 Nov
River Valley Inn
An outdoor patio with white chairs and tables, a central fire feature, and string lights.
A hotel with a sign reading "D. HOTEL & SUITES" on the facade.
A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.
A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
S$182
includes taxes & fees
26 Oct - 27 Oct
D. Hotel Suites & Spa
A hotel lobby with a bar area, dining tables, and comfortable seating.
A lobby with two armchairs, a fireplace, and a framed picture on the wall.
A large, multi-story hotel with a covered entrance and a parking lot.
A deck with a table and chairs, a large umbrella, and a view of a lawn and trees.

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
Hadley
S$191
includes taxes & fees
29 Oct - 30 Oct
Hampton Inn Hadley-Amherst Area
A view of a red building by a waterway through a window.
A yellow multi-story building with a water feature in front.
A wooden porch with a sign reading "OLD MILL" above a double door.
A bar area with wooden stools, a long counter, and potted plants.

Old Mill Inn

Old Mill Inn
Hatfield
S$257
includes taxes & fees
3 Nov - 4 Nov
Old Mill Inn
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chesterfield attractions

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.
See properties

Chesterfield Gorge Reservation

You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
See properties

Chesterfield Town Hall

After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.
See properties

Chesterfield Public Library

Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
See properties

Oak Hill

Commune with nature and explore the great outdoors at Oak Hill during your travels in Chesterfield. Amble around the area's parks or visit its shops.
See properties

Krug Sugarbush

You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.
See properties

Top Chesterfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"We really enjoyed our stay at Berkshire Mountain Lodge. For what we paid - we absolutely feel like we got a great bang for our buck. The hotel is clean and well-maintained, and our suite was massive. It included a kitchen with all the bells and whistles (stove/stovetop, microwave, refrigerator, dishwasher), a full size living room, separate bedroom (with a kingsize mattress), and spacious bathroom. It was so comfortable. We absolutely recommend staying here, especially if you're looking for a reasonably priced accommodation."
Matthew 3-night trip
Posted 2 hours ago
Berkshire Mountain Lodge
Hotel UMass

Hotel UMass

8/10 Good
"Big comfortable room, with a comfy bed. I liked the UMass throw and cushion, I would have wanted to bring it home as a souvenir! Nice continental breakfast with a large range of coffee and juice offer. Love the covered parking. Staff was professional and kind. The bedhead was so used that the leather was peeling and the lampshade was very stained, but everything else was perfect."
Catherine 1-night trip
Posted 2 hours ago
Hotel UMass
D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"The Delaney House Restaurant attached to the hotel was outstanding. Nice atmosphere, good food at reasonable prices."
JOHN 1-night trip
Posted 3 hours ago
D. Hotel Suites & Spa
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

8/10 Good
"The hotel is a great place to stay for a trip in this area."
Ni-Ling 3-night trip
Posted 4 hours ago
Quality Inn & Suites Northampton - Amherst
Hotel On North

Hotel On North

10/10 Excellent
"This is a great hotel.. likely the best place to stay in Pittsfield. Just an overnight stop so not time to get a good read on the area but a good option for the Berkshires if you you don't want to pay the Lenox/Stockbridge premium."
John 1-night trip
Posted 15 hours ago
Hotel On North
Red Roof Inn PLUS+ South Deerfield โ€“ Amherst

Red Roof Inn PLUS+ South Deerfield โ€“ Amherst

8/10 Good
"no breakfast"
Jason 4-night trip
Posted 1 day ago
Red Roof Inn PLUS+ South Deerfield โ€“ Amherst
Riverdale Inn

Riverdale Inn

8/10 Good
"To be honest, I wasn't expecting much. But to my surprise, everything was just fine. The room was clean, the bed was comfortable and the shower had hot water. I would stay again"
Brian 1-night trip
Posted 2 days ago
Riverdale Inn
Inn on Boltwood

Inn on Boltwood

10/10 Excellent
"We had an a very nice stay. Lovely accommodations The staff is top notch. They were always polite, professional and helpful. The grounds are well manicured and lovely. The inn is conveniently located and within walking distance to downtown. We would return."
Jan 2-night trip
Posted 3 days ago
Inn on Boltwood
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"It was pretty clean, and the bed linens was great"
Renata 1-night trip
Posted 5 days ago
Tru by Hilton Chicopee Springfield

More cheap stays in Chesterfield

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
S$155
18 Oct - 19 Oct
includes taxes & fees
Quality Inn West Springfield
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA
S$157
25 Oct - 26 Oct
includes taxes & fees
Blue A Modern Hotel, an Ascend Collection Hotel
Hotel UMass

Hotel UMass

1 Campus Center Way Amherst MA
S$159
9 Nov - 10 Nov
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
Hotel UMass
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

400 Russell St Hadley MA
S$169
4 Nov - 5 Nov
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Comfort Inn & Suites Hadley - Amherst
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA
S$175
9 Nov - 10 Nov
includes taxes & fees
7.2/10 Good! (1,005 reviews)
Quality Inn & Suites Northampton - Amherst
Hampton Inn West Springfield

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA
S$186
1 Nov - 2 Nov
includes taxes & fees
Hampton Inn West Springfield

Frequently asked questions

Where is the best place to stay in Chesterfield?
Located 21.7 mi (34.9 km) from the heart of Chesterfield, Berkshire Mountain Lodge is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are D. Hotel Suites & Spa and Hampton Inn West Springfield. See all available top hotels, or vacation rentals in Chesterfield.
If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?
Yes, you'll find most hotel room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.
What is staying in Chesterfield like?
Visitors can enjoy all that Chesterfield has to offer, including the restaurants, shopping and parks. In Chesterfield, there are 3 hotels and other accommodation options to choose from. Find out more about Chesterfield.
What should I do while I'm visiting Chesterfield?
Natural beauty is on display at Chesterfield Gorge, Oak Hill and Knightville Dam & Reservation. A couple of additional sights to add to your itinerary are Chesterfield Public Library and Chesterfield Town Hall. Take a look at what more there is to see and do in Expedia's Chesterfield guide.
What's the seasonal weather in Chesterfield?
The hottest months are usually July and August, with an average temperature of 20ยฐC, while the coldest months are January and February, with an average of -1ยฐC. The snowiest months in Chesterfield are January, February, November and March, with each month seeing an average of 16 cm of snowfall.

Explore a world of travel with Expedia