𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chesterfield (2026)

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Go beyond your typical stay in Chesterfield

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Our top choices for Chesterfield hotels

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 modern hotel room with a bed, sofa, dining table, and chairs.

1. The Ellery

Northampton

Travis

S$181

includes taxes & fees

28 Oct - 29 Oct

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

A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.

2. Hotel Northampton

Northampton

Beth

S$212

includes taxes & fees

20 Oct - 21 Oct

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

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

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

A bathroom with a toilet, a shower, and a towel rack.

3. River Valley Inn

West Hatfield

Michael

S$120

includes taxes & fees

1 Nov - 2 Nov

A gaming area with arcade machines, a seating area with tables and chairs, and large windows providing natural light.

A hotel room with a television displaying a football game, a desk with a lamp, a microwave, and a refrigerator.

A hotel room with a dining table, two chairs, a sofa, a small table, a lamp, and a kitchenette.

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

4. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

Edward

S$128

includes taxes & fees

1 Nov - 2 Nov

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 multi-story hotel with a parking lot in front.

A hotel with a covered entrance, multiple floors, and a flagpole.

5. Comfort Inn & Suites Hadley - Amherst

Hadley

John

S$169

includes taxes & fees

4 Nov - 5 Nov

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

A reception area with a counter, a refrigerator stocked with snacks, and a wall with a tree pattern.

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.

6. Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

Nancy

S$206

includes taxes & fees

1 Nov - 2 Nov

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 lobby with two armchairs, a fireplace, and a framed picture on the wall.

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

7. Hampton Inn Hadley-Amherst Area

Hadley

Esther

S$191

includes taxes & fees

29 Oct - 30 Oct

An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.

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

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.

8. Courtyard by Marriott Hadley Amherst

Hadley

Yuki

S$205

includes taxes & fees

28 Oct - 29 Oct

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

A yellow multi-story building with a water feature in front.

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

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

9. Old Mill Inn

Hatfield

John

S$257

includes taxes & fees

3 Nov - 4 Nov

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 hotel room with two beds, a microwave, a small table with a phone and a coffee maker, a sink, and a large window with curtains.

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

10. Quality Inn & Suites Northampton - Amherst

Northampton

Glenn

S$175

includes taxes & fees

8 Nov - 9 Nov

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 dining room with a wooden table, chairs, a chandelier, and a fireplace.

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

11. Blooming Inn

Shelburne Falls

Robert

S$161

includes taxes & fees

4 Nov - 5 Nov

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

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

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

12. Quality Inn Lee - Lenox South

Lee

Christine

S$133

includes taxes & fees

2 Nov - 3 Nov

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

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

A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.

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

13. D. Hotel Suites & Spa

Holyoke

Jim

S$182

includes taxes & fees

26 Oct - 27 Oct

An outdoor patio area with a circular fire pit surrounded by wicker chairs and tables.

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

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

A modern kitchen with a built-in microwave, stainless steel refrigerator, and a wooden cabinet above the sink.

14. TownePlace Suites by Marriott Hadley Amherst

Hadley

Sarah

S$225

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a fireplace, red curtains, and a wooden dining table.

A modern hotel lobby with a large TV screen displaying the hotel name, red chairs, wooden shelves, and a clock on the wall.

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.

15. Hotel UMass

Amherst

Darrell

S$159

includes taxes & fees

9 Nov - 10 Nov

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

Pittsfield

Ginger

S$142

includes taxes & fees

10 Nov - 11 Nov

A breakfast area with a waffle station, coffee machine, and various food options.

A modern hotel room with a large bed, a desk, and a chair.

A fitness room with treadmills, an elliptical, and a stationary bike.

17. Tru by Hilton Chicopee Springfield

Chicopee

Gary

S$159

includes taxes & fees

1 Nov - 2 Nov

A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.

A spacious lobby with a reception desk, a blue decorative wall, and a wooden floor.

An indoor swimming pool with clear signage, a no diving policy, and a seating area with chairs and a table.

A hotel lobby with a seating area, a bar, and a TV screen.

18. Fairfield Inn & Suites Springfield Holyoke

Holyoke

Caroline

S$181

includes taxes & fees

1 Nov - 2 Nov

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

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 kitchen with stainless steel appliances, a microwave, and a dishwasher. There is a dining area with a table and chairs.

19. Homewood Suites by Hilton Hadley Amherst

Hadley

Rebecca

S$222

includes taxes & fees

1 Nov - 2 Nov

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

20. Blue A Modern Hotel, an Ascend Collection Hotel

West Springfield

Charles

S$157

includes taxes & fees

25 Oct - 26 Oct

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Hotels recommended for families in Chesterfield

The Ellery

Northampton

S$181

includes taxes & fees

28 Oct - 29 Oct

River Valley Inn

West Hatfield

S$120

includes taxes & fees

1 Nov - 2 Nov

Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

S$128

includes taxes & fees

1 Nov - 2 Nov

Hotel Northampton

Northampton

S$212

includes taxes & fees

20 Oct - 21 Oct

Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

S$206

includes taxes & fees

1 Nov - 2 Nov

Blooming Inn

Shelburne Falls

S$161

includes taxes & fees

4 Nov - 5 Nov

Comfort Inn & Suites Hadley - Amherst

Hadley

S$169

includes taxes & fees

4 Nov - 5 Nov

Hampton Inn Hadley-Amherst Area

Hadley

S$191

includes taxes & fees

29 Oct - 30 Oct

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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.

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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.

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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.

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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.

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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.

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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.

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Top Chesterfield Hotel Reviews

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."

Berkshire Mountain Lodge

10/10 Excellent

"The room was fantastic. Great place to stay in the Berkshires. The hot tub wasn't working, but things happen. Other than that, it was a perfect stay."

Hotel UMass

10/10 Excellent

"Great"

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good

"no breakfast"

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"