Chesterfield Holiday Rentals, Massachusetts: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Chesterfield

Pet friendly

Apartment

Condo

Pool

Family friendly

Hot tub

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chesterfield hotels

A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.

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.

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

1. Hotel Northampton

Northampton

Beth

3.842.141 ₫

4.291.555 ₫ total

includes taxes & fees

20 Oct - 21 Oct

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.

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.

2. Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

Nancy

3.716.656 ₫

4.151.505 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

2.177.213 ₫

2.431.947 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

4. The Ellery

Northampton

Travis

3.276.815 ₫

3.660.202 ₫ total

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.

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

A modern living room with a grey sofa, a red drum, and a kitchen area with wooden cabinets and a microwave.

An indoor swimming pool with clear signage, a lifeguard chair, and a no diving warning.

5. Comfort Inn & Suites Hadley - Amherst

Hadley

John

3.225.846 ₫

3.603.269 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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.

6. Quality Inn & Suites Northampton - Amherst

Northampton

Ni-Ling

3.166.855 ₫

3.537.376 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

7. Hampton Inn Hadley-Amherst Area

Hadley

Esther

3.122.871 ₫

3.488.246 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

8. D. Hotel Suites & Spa

Holyoke

JOHN

3.147.062 ₫

3.682.408 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

9. Old Mill Inn

Hatfield

John

4.643.635 ₫

5.186.941 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

A modern hotel with a covered entrance, outdoor seating, and a brick facade.

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

10. TownePlace Suites by Marriott Hadley Amherst

Hadley

Sarah

4.075.515 ₫

4.552.350 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

11. Courtyard by Marriott Hadley Amherst

Hadley

Yuki

3.702.426 ₫

4.135.611 ₫ total

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 Red Roof Plus hotel with a modern facade, a parking lot, and a landscaped entrance area.

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

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

12. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

Jack

2.310.459 ₫

2.580.783 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

13. Fairfield Inn & Suites Springfield Holyoke

Holyoke

Caroline

3.276.815 ₫

3.660.202 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A spacious living room with a fireplace, comfortable seating, and elegant chandeliers.

14. Inn on Boltwood

Amherst

pam

3.554.950 ₫

3.970.879 ₫ total

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 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.

A modern hotel with a brick facade, multiple windows, and a well-lit entrance.

15. Homewood Suites by Hilton Hadley Amherst

Hadley

Danielle

4.009.798 ₫

4.478.943 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel room with a large bed, bedside tables, a wardrobe, and a mirror.

A swimming pool with a blue interior, surrounded by red chairs and a green bench.

A laundry area with a washing machine and dryer, a wooden shelf, and a wall with text instructions.

16. Tru by Hilton Chicopee Springfield

Chicopee

Gary

2.836.974 ₫

3.218.547 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

17. Hampton Inn & Suites Greenfield

Greenfield

Robert

4.985.727 ₫

5.569.057 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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 modern dining area with tables and chairs, a patterned carpet, and a wall-mounted TV.

A snack and beverage display area with shelves stocked with chips and a refrigerated section with bottled water and soda.

18. Hampton Inn Westfield

Westfield

Shaleen

3.056.895 ₫

3.414.551 ₫ total

includes taxes & fees

16 Nov - 17 Nov

A Best Western hotel with a modern design, featuring a large building with multiple windows and a well-lit entrance.

A gym with treadmills, elliptical machines, and weight benches.

A restaurant with a counter, seating area, and various food and drink dispensers.

A hotel lobby with a brown sofa, a reception desk, a wall-mounted TV, and a large plant.

19. Best Western Springfield West Inn

West Springfield

Susan

2.574.800 ₫

2.946.858 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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.

20. Quality Inn Lee - Lenox South

Lee

Lucinda

2.397.133 ₫

2.677.598 ₫ total

includes taxes & fees

5 Nov - 6 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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 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

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

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

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

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

D. Hotel Suites & Spa

10/10 Excellent

"I have stayed there several times and it is a great place. The staff is wonderful and the hotel is very clean. It is a great get away from every day life. The spa is great and the hot tub and pool are also a great feature. The gym is also an added plus. I would highly recommend this hotel to anyone who is in town."

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!"

More cheap stays in Chesterfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

2.438.013 ₫

2.790.305 ₫ total

30 Oct - 31 Oct

includes taxes & fees

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA

2.617.054 ₫

2.995.220 ₫ total

16 Nov - 17 Nov

includes taxes & fees

9.2/10 Wonderful! (366 reviews)

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

2.836.974 ₫

3.246.917 ₫ total

16 Nov - 17 Nov

includes taxes & fees

8.2/10 Very good! (1,002 reviews)

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

3.166.855 ₫

3.537.376 ₫ total

8 Nov - 9 Nov

includes taxes & fees

7.2/10 Good! (1,000 reviews)

Comfort Inn & Suites Hadley - Amherst

400 Russell St Hadley MA

3.225.846 ₫

3.603.269 ₫ total

16 Nov - 17 Nov

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Hotel UMass

1 Campus Center Way Amherst MA

Get rates

Hotels in Chesterfield with star rating

Frequently asked questions

What's the seasonal weather in Chesterfield?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterfield are January, February, November and March, with each month seeing an average of 16 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Chesterfield on Expedia.com

Find hotels in Chesterfield, MA from 2.431.947 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chesterfield

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chesterfield hotels

1. Hotel Northampton

2. Fairfield Inn & Suites Springfield Northampton/Amherst

3. River Valley Inn

4. The Ellery

5. Comfort Inn & Suites Hadley - Amherst

6. Quality Inn & Suites Northampton - Amherst

7. Hampton Inn Hadley-Amherst Area

8. D. Hotel Suites & Spa

9. Old Mill Inn

10. TownePlace Suites by Marriott Hadley Amherst

11. Courtyard by Marriott Hadley Amherst

12. Red Roof Inn PLUS+ South Deerfield – Amherst

13. Fairfield Inn & Suites Springfield Holyoke

14. Inn on Boltwood

15. Homewood Suites by Hilton Hadley Amherst

16. Tru by Hilton Chicopee Springfield

17. Hampton Inn & Suites Greenfield

18. Hampton Inn Westfield

19. Best Western Springfield West Inn

20. Quality Inn Lee - Lenox South

Stay near popular Chesterfield attractions

Chesterfield Gorge

Chesterfield Gorge Reservation

Chesterfield Town Hall

Chesterfield Public Library

Oak Hill

Krug Sugarbush

Top Chesterfield Hotel Reviews

D. Hotel Suites & Spa

Red Roof Inn PLUS+ West Springfield

Hotel On North

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

River Valley Inn

Hampton Inn West Springfield

Quality Inn West Springfield

Comfort Inn & Suites Hadley - Amherst

The Ellery

More cheap stays in Chesterfield

Quality Inn West Springfield

Blue A Modern Hotel, an Ascend Collection Hotel

Hampton Inn West Springfield

Quality Inn & Suites Northampton - Amherst

Comfort Inn & Suites Hadley - Amherst

Hotel UMass

Hotels in Chesterfield with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app