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

2. River Valley Inn

River Valley Inn
West Hatfield
United States
Michael
CA $120
CA $134 total
includes taxes & fees
Nov 1 - Nov 2
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 hotel room with a bed, a desk, a chair, a television, and framed pictures on the wall.
A lobby with two armchairs, a fireplace, and a framed picture on the wall.

3. Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
Hadley
United States
Esther
CA $191
CA $213 total
includes taxes & fees
Nov 9 - Nov 10
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.
A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.
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 $237 total
includes taxes & fees
Oct 14 - Oct 15
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 $128
CA $142 total
includes taxes & fees
Nov 1 - Nov 2
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 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.
An indoor swimming pool with clear glass walls, a poolside seating area, and a reception desk.

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.
An indoor swimming pool with clear signage, a lifeguard chair, and a no diving warning.
A fitness room with treadmills, an elliptical, and a stationary bike, equipped with digital displays and a wall-mounted TV.

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

9. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
Northampton
United Kingdom
Glenn
CA $175
CA $195 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn & Suites Northampton - Amherst
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 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.

10. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Jim
CA $174
CA $203 total
includes taxes & fees
Oct 26 - Oct 27
D. Hotel Suites & Spa
A breakfast area with a waffle station, coffee machine, and various food options.
A modern hotel building with a prominent 'tru' logo, multiple floors, and a covered entrance area.
Pool
A modern hotel building with a parking lot and a green landscape.

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 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.

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

13. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
CA $132
CA $148 total
includes taxes & fees
Nov 3 - Nov 4
Quality Inn Lee - Lenox South
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 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 $167
CA $188 total
includes taxes & fees
Oct 25 - Oct 26
Hotel UMass
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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A snack bar with shelves of snacks and a refrigerated display.

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 11 - Nov 12
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.
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 reception desk, seating area, and large windows.
A spacious lobby with a reception desk, a blue decorative wall, and a wooden floor.

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

17. Blooming Inn

Blooming Inn
Shelburne Falls
United States
Robert
CA $93
CA $174 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.
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.

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 8 - Nov 9
TownePlace Suites by Marriott Hadley Amherst
An indoor swimming pool with blue walls, large windows, and several lounge chairs.
A modern hotel lobby with a dining area, seating, and a TV screen on the wall.
A snack display with various packaged foods and a microwave.
A Hampton Inn hotel with a modern design, featuring a large entrance, a well-lit parking area, and multiple flags.

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 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
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.
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.
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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

Blue A Modern Hotel, an Ascend Collection Hotel

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!"
Alexander 3-night trip
Posted less than an hour ago
Blue A Modern Hotel, an Ascend Collection Hotel
D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"We loved our stay. The housekeeping and amenities were too notch. Perfect family-friendly hotel near the Yankee Candle Factory."
Sarah 2-night trip
Posted 1 hour ago
D. Hotel Suites & Spa
Quality Inn West Springfield

Quality Inn West Springfield

10/10 Excellent
"A plus"
JOHN 2-night trip
Posted 1 hour ago
Quality Inn West Springfield
Hotel On North

Hotel On North

10/10 Excellent
"Beautiful property, spacious room. Easy parking"
Diana 1-night trip
Posted 4 hours ago
Hotel On North
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 5 hours 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 8 hours ago
Berkshire Mountain Lodge
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 9 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 10 hours ago
Quality Inn & Suites Northampton - 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

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
7.2/10 Good! (1,002 reviews)
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
9.2/10 Wonderful! (365 reviews)
Blue A Modern Hotel, an Ascend Collection Hotel
Hotel UMass

Hotel UMass

1 Campus Center Way Amherst MA
CA $167
CA $188 total
Oct 25 - Oct 26
includes taxes & fees
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 8 - Nov 9
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 $134 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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