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Tonight
29 Aug - 30 Aug
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30 Aug - 31 Aug
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4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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Our top choices for Chesterfield hotels

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 bathtub, toilet, and shower curtain.

1. River Valley Inn

River Valley Inn
West Hatfield
United States
Michael
NZ$168
includes taxes & fees
29 Sept - 30 Sept
River Valley Inn
A hotel lobby with a bar area, dining tables, and comfortable seating.
A large, multi-story hotel with a covered entrance and a parking lot.
A hotel room with a bed, a desk, a chair, a television, and framed pictures on the wall.
A deck with a table and chairs, a large umbrella, and a view of a lawn and trees.

2. Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
Hadley
United States
SHAWN
NZ$246
includes taxes & fees
27 Sept - 28 Sept
Hampton Inn Hadley-Amherst Area
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 modern hotel room with a bed, sofa, dining table, and chairs.

3. The Ellery

The Ellery
Northampton
United States
Holly
NZ$279
includes taxes & fees
14 Sept - 15 Sept
The Ellery
A hotel lobby with a stone wall, leather chairs, a reception desk, and a sign indicating free Wi-Fi in all rooms.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A hotel room with a wooden floor, a leather sofa, a desk with a TV, a dining table with chairs, and a mirror on the wall.
A hotel room with a TV mounted on a wooden cabinet, a microwave, a coffee maker, and a desk with a chair.

4. Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
South Deerfield
United States
Katie
NZ$185
includes taxes & fees
8 Sept - 9 Sept
Red Roof Inn PLUS+ South Deerfield – 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 bar area with a wooden counter, bar stools, and a variety of bottles and glasses.

5. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Kerri
NZ$239
includes taxes & fees
8 Sept - 9 Sept
D. Hotel Suites & Spa
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 lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
A hotel room with two beds, a TV, a desk, and a chair.

6. Hotel Northampton

Hotel Northampton
Northampton
United States
steven
NZ$279
includes taxes & fees
30 Aug - 31 Aug
Hotel Northampton
A view of a red building by a waterway through a window.
A modern living room with a wooden dining table, leather sofa, and a large window.
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.

7. Old Mill Inn

Old Mill Inn
Hatfield
United States
Jeffrey
NZ$339
includes taxes & fees
30 Aug - 31 Aug
Old Mill Inn
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 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.

8. Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
Northampton
Canada
rob
NZ$285
includes taxes & fees
13 Sept - 14 Sept
Fairfield Inn & Suites Springfield Northampton/Amherst
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.

9. Hotel UMass

Hotel UMass
Amherst
United States
Kathryn
NZ$208
includes taxes & fees
20 Sept - 21 Sept
Hotel UMass
A hotel with a covered entrance, a flag, and a sign.
A spacious living area with a fireplace, sofas, and a coffee table.
A hotel room with a bed, a sofa, a round coffee table, and a nightstand.
A hotel room with a sofa, a small table, a red stool, a kitchenette, and a bed.

10. Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
Hadley
United States
Mutharaju Ram Mohan
NZ$274
includes taxes & fees
20 Sept - 21 Sept
Comfort Inn & Suites Hadley - Amherst
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 hotel lobby with a reception desk, seating area, and a large aquarium.

11. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
Northampton
United States
Sara
NZ$249
includes taxes & fees
27 Sept - 28 Sept
Quality Inn & Suites Northampton - Amherst
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.

12. TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
Hadley
United States
Nathan
NZ$362
includes taxes & fees
8 Sept - 9 Sept
TownePlace Suites by Marriott Hadley Amherst
A hotel lobby with a reception desk, seating area, and a dining section.
A gym with treadmills, an elliptical, a stationary bike, and a bench press.
A snack and beverage display area with shelves stocked with chips and a refrigerated section with bottled water and soda.
A hotel room with two beds, a desk, a chair, a lamp, and a window with a view.

13. Hampton Inn Westfield

Hampton Inn Westfield
Westfield
United States
Mykola
NZ$233
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn Westfield
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 large brick building with a prominent entrance and a covered porch area.
A dining area with a wooden table set for four, surrounded by chairs.

14. Black Walnut Inn

Black Walnut Inn
North Amherst
United States
Kelly
NZ$331
includes taxes & fees
14 Sept - 15 Sept
Black Walnut Inn
An indoor swimming pool with clear water, surrounded by windows with a view of trees.
A breakfast area with a sign reading 'HAPPY BREAKFAST STARTS HERE.'
A hotel with a large entrance, a sign reading 'Hampton Inn & Suites,' and a parking lot.
A hotel lobby with a fireplace, seating area, and large windows.

15. Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
Greenfield
United States
Matthew
NZ$341
includes taxes & fees
30 Aug - 31 Aug
Hampton Inn & Suites Greenfield
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.

16. Inn on Boltwood

Inn on Boltwood
Amherst
United States
Starling
NZ$344
includes taxes & fees
20 Sept - 21 Sept
Inn on Boltwood
A modern hotel lobby with a seating area, a fireplace, and a television mounted on a stone wall.
A modern hotel with a brick facade, multiple windows, and a well-lit entrance.
A modern kitchen with stainless steel appliances, a microwave, and a dishwasher. There is a dining area with a table and chairs.
An outdoor seating area with chairs and tables, a covered patio with string lights, and potted plants.

17. Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
Hadley
United States
Doreen
NZ$322
includes taxes & fees
8 Sept - 9 Sept
Homewood Suites by Hilton Hadley Amherst
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 seating area, a bar, and a TV screen.
A spacious lobby with a reception desk, a blue decorative wall, and a wooden floor.

18. Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
Holyoke
United States
Michael
NZ$246
includes taxes & fees
13 Sept - 14 Sept
Fairfield Inn & Suites Springfield Holyoke
A neatly arranged hotel room with a bed, a chair, a desk, and two framed pictures on the wall.
A hotel room with a bed, a chair, a lamp, and a window with curtains.
A wooden sign with 'RESTAURANT RECEPTION ENTRANCE' and an arrow pointing right.
A living room with a sofa, a coffee table, a television, a fireplace, a cabinet, and a lamp.

19. Deerfield Inn

Deerfield Inn
Deerfield
United States
Jonathan
NZ$487
includes taxes & fees
29 Sept - 30 Sept
Deerfield Inn

20. Homewood Suites by Hilton Holyoke-Springfield/North

Homewood Suites by Hilton Holyoke-Springfield/North
Holyoke
United States
Andrew
NZ$262
includes taxes & fees
13 Sept - 14 Sept
Homewood Suites by Hilton Holyoke-Springfield/North
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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.
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

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

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

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

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

Top Chesterfield Hotel Reviews

Recent Reviews in Chesterfield

Hotel UMass

Hotel UMass

8/10 Good
"Stayed there just before move in day as our son goes the other college in town, so it wasn't crowded or noisy. It's worth knowing that the hotel lobby is on the 3rd floor and the floors above are hotel rooms. The floors below are for the students. Walls seem thin as it was easy to overhear conversation in the nearby rooms."
Michael 1-night trip
Posted 1 hour ago
Hotel UMass
Inn on Boltwood

Inn on Boltwood

10/10 Excellent
"It was charming, quiet( even though it was sold out). Downtown Amherst so plenty of places to go for coffee and food."
Laura 1-night trip
Posted 2 hours ago
Inn on Boltwood
Hotel Northampton

Hotel Northampton

10/10 Excellent
"Lovely, central hotel. Highly recommend."
Rachel 1-night trip
Posted 3 hours ago
Hotel Northampton
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"the good….full kitchen, living room, king bedroom, clean bathroom, VERY reasonable nightly rate, especially for central berkshire county in the summer. there is no daily room cleaning, but extra towels, etc are always available from the front desk… the less than good…we’ve stayed here now u time in the past 18 months, but the last couple of stays the rooms have been a little musty and damp, despite (or because of?) the a/c being on constantly. ya gotta hold the handle down on the toilet to get a complete flush. no food service, but the is a stop&shop literally across the street… i would still recommend BML for the room rate and location alone…"
Barry 2-night trip
Posted 3 hours ago
Berkshire Mountain Lodge
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"You need dimmer switches for lighting over the beds!"
Annie 1-night trip
Posted 21 hours ago
Tru by Hilton Chicopee Springfield
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

10/10 Excellent
"Very good and comfortable place to stay."
Mutharaju Ram Mohan 1-night trip
Posted 1 day ago
Comfort Inn & Suites Hadley - Amherst
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"
Corinne 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

8/10 Good
"Staff extremely helpful and pleasant. Loved the room. Comfy beds. Loved having the kitchenette. The pool was nice; the jacuzzi was colder than the pool. But pool was a lovely temp. The only downside was we could hear then people walking above us at like 3 am. Walls and ceilings may be a tad thin. However, very pleasant experience. Very reasonable price and was perfect for our stay to be near Six Flags."
Ashley 2-night trip
Posted 4 days ago
Candlewood Suites West Springfield by IHG
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 8 days ago
FairBridge Inn Express

More cheap accommodation in Chesterfield

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
NZ$110
30 Aug - 31 Aug
includes taxes & fees
FairBridge Inn Express
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street West Springfield MA
NZ$170
7 Sept - 8 Sept
includes taxes & fees
Red Roof Inn PLUS+ West Springfield
Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
NZ$171
8 Sept - 9 Sept
includes taxes & fees
Quality Inn West Springfield
Hotel UMass

Hotel UMass

1 Campus Center Way Amherst MA
NZ$208
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Hotel UMass
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
NZ$221
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (176 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA
NZ$249
27 Sept - 28 Sept
includes taxes & fees
7.2/10 Good! (1,005 reviews)
Quality Inn & Suites Northampton - Amherst

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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 can I save on a hotel booking in Chesterfield with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Chesterfield hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Chesterfield?
Prices for hotels in Chesterfield often vary, but you can find a great deal from NZ$110 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 our cheapest rates.

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