Hotels in Chesterfield

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Where to stay in Chesterfield?

A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

A hotel room with two beds, a sofa, a desk, a TV, and a picture on the wall.

A bathroom with a bathtub, toilet, and shower curtain.

A row of single-story motel buildings with a parking lot in front.

1. River Valley Inn

West Hatfield

$84

$94 total

includes taxes & fees

Nov 1 - Nov 2

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

A modern hotel room with a dining area, a sofa, a bed, and a TV.

A brick building with a sign reading "The Ellery."

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.

2. The Ellery

Northampton

$127

$141 total

includes taxes & fees

Nov 1 - Nov 2

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.

3. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

$89

$100 total

includes taxes & fees

Nov 1 - Nov 2

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 a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.

A hotel room with two beds, a TV, a desk, and a chair.

An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.

4. Hotel Northampton

Northampton

$165

$184 total

includes taxes & fees

Oct 27 - Oct 28

A hotel lobby with a bar area, dining tables, and comfortable seating.

A deck with a table and chairs, a large umbrella, and a view of a lawn and trees.

A hotel room with a bed, a desk, a chair, a television, and framed pictures on the wall.

A large, multi-story hotel with a covered entrance and a parking lot.

5. Hampton Inn Hadley-Amherst Area

Hadley

$121

$135 total

includes taxes & fees

Nov 15 - Nov 16

A two-story house with a porch, a balcony, and a chimney.

A traditional living room with a green sofa, a yellow armchair, a wooden coffee table, and a patterned rug.

A bedroom with floral wallpaper, a bed, a dresser, a vanity, a chair, and a window with curtains.

A traditional dining room with a wooden table, chairs, and a chandelier.

6. Blooming Inn

Shelburne Falls

$73

$131 total

includes taxes & fees

Oct 18 - Oct 19

A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.

An indoor swimming pool with clear glass walls, a poolside seating area, and a reception desk.

A modern hotel dining area with multiple tables and chairs, pendant lighting, and a view of the city through large windows.

A Fairfield by Marriott hotel with a modern entrance, American flags, and a stone facade.

7. Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

$144

$160 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

8. Quality Inn Lee - Lenox South

Lee

$93

$103 total

includes taxes & fees

Nov 5 - Nov 6

A view of a red building by a waterway through a window.

A bar area with wooden stools, a long counter, and potted plants.

A wooden porch with a sign reading "OLD MILL" above a double door.

A modern living room with a wooden dining table, leather sofa, and a large window.

9. Old Mill Inn

Hatfield

$179

$200 total

includes taxes & fees

Nov 3 - Nov 4

A modern restaurant with high tables and bar stools, a fireplace, and a TV mounted on the wall.

A room with a grey sofa, a small table, a lamp, a door, and a framed abstract artwork on the wall.

A vending machine stocked with snacks and beverages, and shelves with packaged goods.

A hotel lobby with a reception desk, seating area, and a large aquarium.

10. Quality Inn & Suites Northampton - Amherst

Northampton

$122

$137 total

includes taxes & fees

Nov 8 - Nov 9

An outdoor patio with white chairs and tables, a central fire feature, and string lights.

A bar area with a wooden counter, bar stools, and a variety of bottles and glasses.

A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

A hotel with a sign reading "D. HOTEL & SUITES" on the facade.

11. D. Hotel Suites & Spa

Holyoke

$135

$158 total

includes taxes & fees

Oct 26 - Oct 27

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.

A hotel with a covered entrance, a flag, and a clear sky.

A hotel room with a desk, chair, TV, and a bed.

12. Comfort Inn & Suites Hadley - Amherst

Hadley

$125

$139 total

includes taxes & fees

Nov 16 - Nov 17

A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".

A spacious outdoor seating area with a fire feature, white brick walls, and multiple windows with shutters.

A modern living room with a sofa, armchairs, a coffee table, and a wine rack.

A long dining table set with white tableware, flanked by windows and a skylight.

13. Inn on Boltwood

Amherst

$137

$153 total

includes taxes & fees

Nov 3 - Nov 4

A modern hotel lobby with a stone wall, a fireplace, a bar area, and seating arrangements.

A modern lounge area with a stone wall, a fireplace, a sofa, and two blue armchairs.

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.

14. Homewood Suites by Hilton Hadley Amherst

Hadley

$155

$173 total

includes taxes & fees

Oct 28 - Oct 29

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.

An indoor swimming pool with clear safety signage, a sunlit area with seating, and a view through large windows.

A modern kitchen with wooden cabinets, a central island with a fruit bowl, and a breakfast bar.

15. TownePlace Suites by Marriott Hadley Amherst

Hadley

$158

$176 total

includes taxes & fees

Nov 8 - Nov 9

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 hotel room with a large bed, two bedside tables with lamps, a massage chair, and a wall mural of mountains.

A modern hotel with a covered entrance, multiple windows, and a well-maintained lawn.

16. Blue A Modern Hotel, an Ascend Collection Hotel

West Springfield

$101

$116 total

includes taxes & fees

Nov 16 - Nov 17

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 conference room with two Dell computers, a large autumn-themed painting, and two wall-mounted lamps.

A dining table set with multiple wine glasses, a centerpiece with flowers, and candles.

17. Courtyard by Marriott Hadley Amherst

Hadley

$143

$160 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern cafe with a counter, seating area, and large windows.

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.

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

Pittsfield

$99

$111 total

includes taxes & fees

Nov 15 - Nov 16

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A spacious lobby with a fireplace, seating area, and a bar.

A garden with wooden Adirondack chairs and a stone pathway.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

19. Berkshire Mountain Lodge

Pittsfield

$95

$128 total

includes taxes & fees

Nov 15 - Nov 16

A room with a bed, a sofa, a coffee table, and a television.

A living room with a round coffee table, a sofa, and a wall art piece.

A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television mounted on the wall.

A large brick building with a prominent entrance and a covered porch area.

20. Black Walnut Inn

North Amherst

$185

$207 total

includes taxes & fees

Oct 27 - Oct 28

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Go beyond your typical stay in Chesterfield

Pet friendly

Pool

Hot tub

Family friendly

Cottage

Top landmarks in Chesterfield

Chesterfield Gorge

Chesterfield Gorge is 2.1 mi (3.4 km) from central Chesterfield, why not stop by during your stay. Want to stretch your legs some more? Head to Chester Wildlife Management Area, located nearby.

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Chesterfield Gorge Reservation

Chesterfield Gorge Reservation is 1.7 mi (2.7 km) from central Chesterfield, why not stop by during your stay.

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Chesterfield Town Hall

Chesterfield Town Hall is worth a visit when in central Chesterfield.

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Chesterfield Public Library

Chesterfield Public Library is worth a visit when in central Chesterfield.

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Oak Hill

If you want to stretch your legs and breathe in some fresh mountain air, head out to Oak Hill for a bird's-eye view of Chesterfield.

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Krug Sugarbush

Krug Sugarbush is 2.1 mi (3.4 km) from central Chesterfield, why not stop by during your stay.

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Check out reviews of Chesterfield hotels guests love

Red Roof Inn PLUS+ West Springfield

10/10 Excellent

"The hotel was close everything very nice Clean staff was accommodating"

Hotel On North

10/10 Excellent

"The hotel is charming in the heart of Pittsfield. The rooms were large and clean. It’s a great boutique hotel with 35 rooms. There is a restaurant attached to the hotel that had great food and drinks! Will definitely be back."

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

10/10 Excellent

"New hotel with clean"

River Valley Inn

8/10 Good

"Enjoyed the stay. Great staff. Good location. Thank You!"

Hampton Inn West Springfield

8/10 Good

"Room was clean, microwave and refrigerator clean and working, staff was friendly and helpful. Breakfast was better than most. The bath however had problems. The water faucet was loose and not connected to the tub and the water control was difficult to pull to start. Tub plug was very hard to use."

Quality Inn West Springfield

10/10 Excellent

"Overall I had a great two day stay at the Quality Inn. I have stayed here over a dozen times when in the area to visit Six Flags, my previous visit was in the spring, and they have made some updates since! I noticed new chairs in the hallways and room, and the exterior of the building was repainted a new color and looks more modern! I had room 421, a 2 queen, which was mostly clean and comfortable. Only issue was the new tan chair by the door looked comfortable, but I did not sit in it, as it had long hairs and sticky residue all over the cushion... Otherwise the room was clean, beds were comfortable with 4 pillows on each bed, lots of towels, and fridge worked great! The lamp between the bed did not work though... At check in, the man with tattoos on his hands wasn't that friendly or welcoming but did honor my request for a higher floor. Later, when returning from dinner next door (Great Japanese restaurant!) I heard him tell a guest she had the entire 5th floor to herself, which was annoying as each night I had neighbors who I could hear easily through the walls... Why not space out guests when there is space? I woke up my first morning to hearing the neighbors talk... Breakfast was fine with a decent variety, I liked the donuts, eggs were decent, as was the sausage. The room was a great value and I will return. It looks like the first floor was restored for guest use again too! Nice to see some changes and hope they continue renovating and updating the property!"

Comfort Inn & Suites Hadley - Amherst

8/10 Good

"Coffee all day."

The Ellery

10/10 Excellent

"Very helpful staff, tastefully decorated, super breakfast, very comfortable bed. We’ll be back!"

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"We had a wonderful stay! The staff were incredibly friendly and welcoming. Everything in the hotel is beautiful, modern, fresh and brand new. We were especially impressed by the complimentary massage chairs in the room. Highly recommend this hotel!"

Frequently asked questions

Can I book refundable hotels in Chesterfield?

If you're looking for the flexibility to change your plans to Chesterfield, most accommodations offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

What will the weather in Chesterfield be like during my visit?

The warmest months in Chesterfield are usually July and August with an average temp of 68°F. January and February are the chilliest months when the average temp is 30°F. The rainiest months are October and July.

Why should I book my Chesterfield accommodation with Hotels.com?

There are plenty of reasons to book your Chesterfield travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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