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Oct 13 - Oct 14
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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 bed, sofa, dining table, and chairs.
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.

1. The Ellery

The Ellery
Northampton
United States
Travis
CA $181
CA $202 total
includes taxes & fees
Oct 28 - Oct 29
The Ellery
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 bathroom with a toilet, a shower, and a towel rack.

2. River Valley Inn

River Valley Inn
West Hatfield
United States
Michael
CA $120
CA $134 total
includes taxes & fees
Nov 3 - Nov 4
River Valley Inn
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 large, multi-story hotel with a covered entrance and a parking lot.

3. Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
Hadley
United States
Esther
CA $191
CA $213 total
includes taxes & fees
Nov 1 - Nov 2
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.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.
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.

4. Hotel Northampton

Hotel Northampton
Northampton
United States
Beth
CA $212
CA $236 total
includes taxes & fees
Oct 20 - Oct 21
Hotel Northampton
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.

5. Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
South Deerfield
United States
Edward
CA $127
CA $142 total
includes taxes & fees
Nov 2 - Nov 3
Red Roof Inn PLUS+ South Deerfield – Amherst
A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.
A Fairfield by Marriott hotel with a modern entrance, American flags, and a stone facade.
A modern hotel dining area with multiple tables and chairs, pendant lighting, and a view of the city through large windows.
A reception area with a counter, a refrigerator stocked with snacks, and a wall with a tree pattern.

6. Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
Northampton
United States
Nancy
CA $205
CA $229 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites Springfield Northampton/Amherst
A swimming pool area with a hot tub, a no diving sign, and a chair near the pool.
A hotel lobby with a bar area, seating arrangements, and an exit sign.
A fitness room with treadmills, an elliptical, and a stationary bike, equipped with digital displays and a wall-mounted TV.
An indoor swimming pool with clear signage, a lifeguard chair, and a no diving warning.

7. Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
Hadley
United States
John
CA $169
CA $189 total
includes taxes & fees
Nov 4 - Nov 5
Comfort Inn & Suites Hadley - 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 conference room with two Dell computers, a large autumn-themed painting, and two wall-mounted lamps.

8. Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
Hadley
United States
Yuki
CA $204
CA $228 total
includes taxes & fees
Oct 29 - Oct 30
Courtyard by Marriott Hadley Amherst
A modern restaurant with high tables and bar stools, a fireplace, and a TV mounted 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 room with a grey sofa, a small table, a lamp, a door, and a framed abstract artwork on the wall.
A hotel lobby with a reception desk, seating area, and a large aquarium.

9. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
Northampton
United Kingdom
Glenn
CA $175
CA $195 total
includes taxes & fees
Nov 10 - Nov 11
Quality Inn & Suites Northampton - Amherst
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 hotel with a sign reading "D. HOTEL & SUITES" on the facade.

10. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Jim
CA $173
CA $203 total
includes taxes & fees
Oct 28 - Oct 29
D. Hotel Suites & Spa
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 modern hotel building with a prominent 'tru' logo, multiple floors, and a covered entrance area.
A modern hotel room with a flat-screen TV on a wooden desk, a blue office chair, and a large window with abstract art.

11. Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
Chicopee
United States
Gary
CA $157
CA $178 total
includes taxes & fees
Nov 1 - Nov 2
Tru by Hilton Chicopee Springfield
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 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.

12. Old Mill Inn

Old Mill Inn
Hatfield
United States
John
CA $256
CA $286 total
includes taxes & fees
Nov 3 - Nov 4
Old Mill Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
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.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

13. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
CA $132
CA $148 total
includes taxes & fees
Nov 2 - Nov 3
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 registration desk with a sign above it, a receptionist, and several people standing in line.
A modern building with a grid-like facade, multiple balconies, and a spacious courtyard with geometric sculptures.

14. Hotel UMass

Hotel UMass
Amherst
United States
Darrell
CA $156
CA $177 total
includes taxes & fees
Nov 9 - Nov 10
Hotel UMass
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
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.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ginger
CA $141
CA $158 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.
A hotel lobby with a reception desk, seating area, and large windows.
A hotel lobby with a seating area, a bar, and a TV screen.
An indoor swimming pool with clear signage, a no diving policy, and a seating area with chairs and a table.

16. Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
Holyoke
United States
Caroline
CA $181
CA $202 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites Springfield Holyoke
A two-story house with a porch, a balcony, and a chimney.
A bedroom with floral wallpaper, a bed, a dresser, a vanity, a chair, and a window with curtains.
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.

17. Blooming Inn

Blooming Inn
Shelburne Falls
United States
Robert
CA $98
CA $180 total
includes taxes & fees
Nov 4 - Nov 5
Blooming Inn
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.

18. TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
Hadley
United States
Sarah
CA $225
CA $251 total
includes taxes & fees
Nov 10 - Nov 11
TownePlace Suites by Marriott Hadley Amherst
An indoor swimming pool with blue walls, large windows, and several lounge chairs.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view.
A Hampton Inn hotel with a modern design, featuring a large entrance, a well-lit parking area, and multiple flags.
A snack display with various packaged foods and a microwave.

19. Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield
Chicopee
United States
Melissa
CA $166
CA $189 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Chicopee/Springfield
A modern lounge area with sofas, a pool table, and a unique 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.
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
CA $153
CA $175 total
includes taxes & fees
Oct 25 - Oct 26
Blue A Modern Hotel, an Ascend Collection Hotel
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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 forest 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.
See properties

Top Chesterfield Hotel Reviews

Hotel Northampton

Hotel Northampton

10/10 Excellent
"Very good. Friendly. And downtown. Thank you!"
Laurent 1-night trip
Posted 1 hour ago
Hotel Northampton
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"Very clean and new hotel."
Glendys Maria 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 3 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 4 hours ago
Hotel UMass
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent
"For me, the location was perfect! The service was very friendly, the price was great, and everything in the room was excellent. Thanks for the wonderful time we had.🤗👏"
Emely 1-night trip
Posted 4 hours ago
Red Roof Inn PLUS+ South Deerfield – Amherst
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 6 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 17 hours ago
Hotel On North
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

More cheap stays in Chesterfield

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
CA $127
CA $145 total
Nov 5 - Nov 6
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
CA $153
CA $175 total
Oct 25 - Oct 26
includes taxes & fees
Blue A Modern Hotel, an Ascend Collection Hotel
Hotel UMass

Hotel UMass

1 Campus Center Way Amherst MA
CA $156
CA $177 total
Nov 9 - Nov 10
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
CA $169
CA $189 total
Nov 4 - Nov 5
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
CA $175
CA $195 total
Nov 10 - Nov 11
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
CA $181
CA $207 total
Nov 10 - Nov 11
includes taxes & fees
Hampton Inn West Springfield

Hotels in Chesterfield with star rating

Frequently asked questions

When is the best time to go to Chesterfield?
The best time to go to Chesterfield is during the autumn months, specifically from late September through October.This period offers stunning natural beauty as the Berkshire Hills transform with vibrant fall foliage. The weather is typically crisp and pleasant, ideal for outdoor activities like hiking, scenic drives, and exploring the local area. You'll find fewer crowds compared to peak summer, allowing for a more relaxed experience.Couples looking for a romantic getaway will particularly enjoy Chesterfield in the autumn. The picturesque landscapes provide a beautiful backdrop for leisurely drives along Route 143 or walks through the Chesterfield Gorge. Many local inns and bed and breakfasts offer cosy amenities, great for a peaceful escape.For travellers interested in outdoor pursuits, the autumn weather is great for exploring the many hiking trails in the surrounding state forests, such as the Knightville Dam area. The cooler temperatures make for comfortable walking, and the changing leaves offer spectacular views.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chesterfield.
How much is the nightly rate at a Chesterfield hotel?
Prices for hotels in Chesterfield often vary, but you can find a great deal from CA $88 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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