Chester Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Chester hotels

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.

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.

1. Fairfield Inn & Suites Springfield Holyoke

Holyoke

Caroline

฿4,256

฿4,753 total

includes taxes & fees

16 Nov - 17 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A covered outdoor area with stone pillars and a view of a road and green hills.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

2. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

฿4,221

฿4,714 total

includes taxes & fees

1 Nov - 2 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 hotel room with two beds, a desk, a chair, a lamp, and a window with a view.

3. Hampton Inn Westfield

Westfield

Shaleen

฿3,970

฿4,434 total

includes taxes & fees

17 Nov - 18 Nov

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.

4. Quality Inn Lee - Lenox South

Lee

Lucinda

฿3,113

฿3,477 total

includes taxes & fees

11 Nov - 12 Nov

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

5. The Yankee Inn

Lenox

Basil

฿3,562

฿3,978 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A room with a foosball table, a sofa, and a wall with various attractions listed.

6. Tru by Hilton Chicopee Springfield

Chicopee

Gary

฿3,379

฿3,833 total

includes taxes & fees

16 Nov - 17 Nov

A multi-story hotel with a prominent 'La Quinta' sign, featuring a symmetrical facade with evenly spaced windows and a central entrance.

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

A hotel dining area with multiple tables and chairs, a patterned carpet, and a reception desk in the background.

A spacious lobby with wooden flooring, a reception desk, and two patterned armchairs.

7. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center

Heather

฿3,684

฿4,180 total

includes taxes & fees

15 Nov - 16 Nov

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.

8. Hampton Inn Chicopee/Springfield

Chicopee

Melissa

฿3,747

฿4,251 total

includes taxes & fees

17 Nov - 18 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

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

A kitchenette with a microwave, coffee maker, and coffee cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

9. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Cynthia

฿3,024

฿3,378 total

includes taxes & fees

12 Nov - 13 Nov

A hotel patio with outdoor seating and a fire pit.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

10. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿4,297

฿4,800 total

includes taxes & fees

1 Nov - 2 Nov

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

11. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

฿4,827

฿5,392 total

includes taxes & fees

2 Nov - 3 Nov

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A dining area with large windows, wooden furniture, and a view of a lake.

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside dock with kayaks and a covered boat ramp.

12. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Gustavo

฿3,856

฿4,307 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

13. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

฿3,279

฿3,662 total

includes taxes & fees

15 Nov - 16 Nov

A patio area with a stone fire pit, wicker furniture, and a view of the building's interior.

A spacious lobby with comfortable seating, a fireplace, and large windows.

A hotel exterior with a sign reading "Residence Inn Marriott."

A spacious hotel lobby with a high ceiling, a fireplace, seating areas, and a large TV screen.

14. Residence Inn Springfield Chicopee

Chicopee

Ronald

฿5,684

฿6,448 total

includes taxes & fees

2 Nov - 3 Nov

An outdoor patio area with seating, a fire feature, and a view of the building's exterior.

A modern bar area with a long counter, multiple screens, and a seating area with metal chairs.

A hotel room with two beds, a large window with a view of trees, and a wall mural.

A modern bar area with a long counter, multiple bar stools, and a wooden accent wall.

15. Courtyard by Marriott West Springfield

West Springfield

Amy

฿4,406

฿5,043 total

includes taxes & fees

15 Nov - 16 Nov

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

A hotel entrance with a covered patio, a garden with colorful flowers, and a clear sky.

A spacious hotel dining area with multiple tables and chairs, a kitchen area, and a high ceiling with natural light.

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

16. Homewood Suites by Hilton Holyoke-Springfield/North

Holyoke

Andrew

฿6,007

฿6,709 total

includes taxes & fees

16 Nov - 17 Nov

A modern lounge area with sofas, a pool table, and a unique chandelier.

A modern coffee bar with espresso machines, a coffee station, and a shelf with coffee products.

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

A modern hotel lobby with blue sofas, a bar area, and a decorative chandelier.

17. Blue A Modern Hotel, an Ascend Collection Hotel

West Springfield

Samantha

฿3,399

฿3,890 total

includes taxes & fees

16 Nov - 17 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A wooden cabinet with a coffee maker and a white container.

18. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

฿3,684

฿4,115 total

includes taxes & fees

30 Oct - 31 Oct

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.

19. The Ellery

Northampton

Travis

฿4,256

฿4,753 total

includes taxes & fees

9 Nov - 10 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A spacious lobby with a fireplace, seating area, and a bar.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

20. Berkshire Mountain Lodge

Pittsfield

ulla

฿2,880

฿3,968 total

includes taxes & fees

22 Nov - 23 Nov

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Stay near popular Chester attractions

Chester Town Hall

You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area.

See properties

Learn more about Chester

Experience the hiking, camping and theatre in Chester!

See all hotels in Chester

A snow-covered forest with a narrow stream running through it.

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Check in & out were easy. Mint restaurant was GREAT. View from the balcony overlooking the lake was super. Same weekend for the last four years & we will be back."

D. Hotel Suites & Spa

10/10 Excellent

"Nice stay will be coming back again!"

The Yankee Inn

8/10 Good

"Efficient & comfortable. Very good value."

Hotel Northampton

10/10 Excellent

"great place and location. twice I felt like I was about to be kicked out, before they realized I was a guest, so that didn't feel great. I can hazard a guess as to why. other than that it's a great building."

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

Quality Inn & Suites Northampton - Amherst

10/10 Excellent

"Excellent and comfortable stay"

Hampton Inn West Springfield

10/10 Excellent

"."

More cheap stays in Chester

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

฿2,919

฿3,341 total

17 Nov - 18 Nov

includes taxes & fees

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street West Springfield MA

฿3,145

฿3,600 total

2 Nov - 3 Nov

includes taxes & fees

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA

฿3,399

฿3,890 total

16 Nov - 17 Nov

includes taxes & fees

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

฿3,456

฿3,955 total

4 Nov - 5 Nov

includes taxes & fees

8.2/10 Very good! (1,000 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,562

฿3,978 total

1 Nov - 2 Nov

includes taxes & fees

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

฿4,099

฿4,578 total

17 Nov - 18 Nov

includes taxes & fees

7.2/10 Good! (1,000 reviews)

Frequently asked questions

What's the best place to stay in Chester?

Berkshire Mountain Lodge, located 17.2 mi (27.7 km) from the heart of Chester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are D. Hotel Suites & Spa and Hampton Inn West Springfield. See all available top hotels, or vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes, the majority of room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer, including the waterfalls, shopping and riverfront. Tourists can also enjoy the city's restaurants, theatres and monuments. There are 887 hotels and other accommodation options in the surrounding area. Find out more about Chester.

What is there to see in Chester?

A favourite place to visit is Chester Town Hall. You'll also find Glendale Falls and Pyramid Lake in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

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Book Hotels in Chester on Expedia.com

Find hotels in Chester, MA from ฿2,456

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

1. Fairfield Inn & Suites Springfield Holyoke

2. Courtyard by Marriott Lenox Berkshires

3. Hampton Inn Westfield

4. Quality Inn Lee - Lenox South

5. The Yankee Inn

6. Tru by Hilton Chicopee Springfield

7. La Quinta Inn & Suites by Wyndham Springfield MA

8. Hampton Inn Chicopee/Springfield

9. Holiday Inn Express Hotel & Suites Great Barrington by IHG

10. Hilton Garden Inn Lenox Pittsfield

11. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

12. The Black Swan Lee - Lenox, an Ascend Collection Hotel

13. Best Western Plus Berkshire Hills Inn & Suites

14. Residence Inn Springfield Chicopee

15. Courtyard by Marriott West Springfield

16. Homewood Suites by Hilton Holyoke-Springfield/North

17. Blue A Modern Hotel, an Ascend Collection Hotel

18. Hampton Inn & Suites Berkshires-Lenox

19. The Ellery

20. Berkshire Mountain Lodge

Stay near popular Chester attractions

Chester Town Hall

Learn more about Chester

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

D. Hotel Suites & Spa

The Yankee Inn

Hotel Northampton

Hotel On North

Quality Inn & Suites Northampton - Amherst

Hampton Inn West Springfield

More cheap stays in Chester

Quality Inn West Springfield

Red Roof Inn PLUS+ West Springfield

Blue A Modern Hotel, an Ascend Collection Hotel

Hampton Inn West Springfield

The Yankee Inn

Quality Inn & Suites Northampton - Amherst

Frequently asked questions

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