Chester Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Chester hotels

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

1. Quality Inn Lee - Lenox South

Lee

Christine

2.397.041 ₫

2.677.494 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

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

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

2. The Yankee Inn

Lenox

Basil

2.742.432 ₫

3.063.296 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A building with a flat roof, multiple windows, and a satellite dish.

A hotel room with a large bed, a chair, a nightstand with a lamp, and a window with blinds.

A kitchen with wooden cabinets, a granite countertop, a stainless steel sink, and a coffee maker.

A dining area with a round table set for four, surrounded by dark chairs. A white door is visible in the background, leading to a kitchen area with white appliances.

3. Becket Motel

Becket

Paul

2.845.920 ₫

4.045.863 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A hotel lobby with a reception desk, seating area, and a dining section.

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

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

A gym with treadmills, an elliptical, a stationary bike, and a bench press.

4. Hampton Inn Westfield

Westfield

Shaleen

3.056.777 ₫

3.414.420 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A calm lake at dusk with a wooden dock and two chairs facing the water.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

A room with two beds, a round mirror, a red box, and a hanging light fixture.

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

5. Berkshire Lake Lodge

Lee

mike

3.667.356 ₫

4.096.436 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

6. Berkshires Untold

Lenox

Madhavi R

3.368.254 ₫

3.762.339 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

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

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

7. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

3.249.782 ₫

3.630.006 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

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

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

Lee

Bob

3.056.777 ₫

3.414.420 ₫ total

includes taxes & fees

10 Nov - 11 Nov

A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.

A hotel lobby with a seating area, a bar, and a TV screen.

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.

9. Fairfield Inn & Suites Springfield Holyoke

Holyoke

MONA

3.386.645 ₫

3.782.883 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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 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

Holyoke

Jim

3.146.941 ₫

3.682.266 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

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

A hotel patio with outdoor seating and a fire pit.

11. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.308.511 ₫

3.695.556 ₫ total

includes taxes & fees

1 Nov - 2 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.

12. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center

Heather

2.858.856 ₫

3.243.373 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A bar with wooden floors and shelves filled with bottles.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

13. The Red Lion Inn

Stockbridge

Stephan

4.075.357 ₫

5.837.494 ₫ total

includes taxes & fees

3 Nov - 4 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 garden with wooden Adirondack chairs and a stone pathway.

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

14. Berkshire Mountain Lodge

Pittsfield

marilyn

2.217.814 ₫

3.055.278 ₫ total

includes taxes & fees

9 Nov - 10 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 reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

15. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

2.418.515 ₫

2.701.481 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern dining area with a high ceiling, large windows, and a mix of wooden and upholstered furniture.

A modern hotel lobby with a reception desk, a coffee machine, a plant, a leather sofa, and a dining area.

A modern office space with a large window overlooking a parking lot and trees.

A Quality Inn by Choice Hotels with a simple, modern design, featuring a prominent sign and a parking lot.

16. Quality Inn Westfield - Springfield

Westfield

Jennifer

2.419.032 ₫

2.702.058 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

17. Hotel Northampton

Northampton

Beth

3.841.992 ₫

4.291.389 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

A fitness room with treadmills, an elliptical, and a stationary bike.

A modern hotel room with a large bed, a desk, and a chair.

A modern hotel room with a flat-screen TV on a wooden desk, a blue office chair, and a large window with abstract art.

18. Tru by Hilton Chicopee Springfield

Chicopee

Laura

2.836.865 ₫

3.218.424 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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

Great Barrington

Kelly

3.716.513 ₫

4.151.345 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

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

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

20. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

2.946.821 ₫

3.291.599 ₫ total

includes taxes & fees

7 Nov - 8 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

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was incredible. Just need to be a little friendly at the arrival."

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"I considered staying 1 more night and it never happened in my life"

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

10/10 Excellent

"We requested a room on the first floor in advance. When we got there there were aware and assigned us accordingly! Staff very accommodating to our questions and food inquiries"

Berkshires Untold

10/10 Excellent

"Great, we'll run hotel"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."

La Quinta Inn & Suites by Wyndham Springfield MA

8/10 Good

"The staff was excellent and very friendly. Always greeted me when I came in the hotel, so the acknowledgement was nice. The room was very clean, but the rug in the hallway had a musty smell to it."

D. Hotel Suites & Spa

10/10 Excellent

"I love this hotel. The fall decorations are adorable. When I checked in the room was clean but there had obviously been a work crew in the bathroom caulking and hadn’t fully cleaned up. I alerted the front desk and was immediately moved to a lovely cleaned suite. The onsite restaurant is also great."

Tru by Hilton Chicopee Springfield

10/10 Excellent

"It was pretty clean, and the bed linens was great"

Quality Inn & Suites Northampton - Amherst

8/10 Good

"They are undergoing some renovations - so beware because the outside isn't looking that great! BUT ... my room was clean/breakfast room was sunny with PLENTY of tables and food/drink options for even the pickiest of eaters. REAL eggs, REAL bacon, too. My bed was AMAZING. I just bought a VERY expensive mattress and this one was better by far! Shower was good/water pressure/temp, too. I was a bit wary when I drove up and parked, and the night clerk was a bit ditzy but the guy on this morning was very nice/helpful. I couldn't have been more pleased with my overall stay. Well done, Quality Inn!"

More cheap stays in Chester

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.606.651 ₫

1.794.629 ₫ total

12 Oct - 13 Oct

includes taxes & fees

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

2.277.253 ₫

2.606.315 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA

2.616.953 ₫

2.995.104 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (359 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.742.432 ₫

3.063.296 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

3.166.733 ₫

3.537.241 ₫ total

8 Nov - 9 Nov

includes taxes & fees

7.2/10 Good! (1,003 reviews)

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

3.276.689 ₫

3.750.170 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Hotels in Chester with star rating

Frequently asked questions

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 1.729.543 ₫

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. Quality Inn Lee - Lenox South

2. The Yankee Inn

3. Becket Motel

4. Hampton Inn Westfield

5. Berkshire Lake Lodge

6. Berkshires Untold

7. Courtyard by Marriott Lenox Berkshires

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

9. Fairfield Inn & Suites Springfield Holyoke

10. D. Hotel Suites & Spa

11. Hilton Garden Inn Lenox Pittsfield

12. La Quinta Inn & Suites by Wyndham Springfield MA

13. The Red Lion Inn

14. Berkshire Mountain Lodge

15. Best Western Plus Berkshire Hills Inn & Suites

16. Quality Inn Westfield - Springfield

17. Hotel Northampton

18. Tru by Hilton Chicopee Springfield

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

20. Hampton Inn & Suites Berkshires-Lenox

Stay near popular Chester attractions

Chester Town Hall

Learn more about Chester

Top Chester Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Blue A Modern Hotel, an Ascend Collection Hotel

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

Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

La Quinta Inn & Suites by Wyndham Springfield MA

D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

Quality Inn & Suites Northampton - Amherst

More cheap stays in Chester

FairBridge Inn Express

Quality Inn West Springfield

Blue A Modern Hotel, an Ascend Collection Hotel

The Yankee Inn

Quality Inn & Suites Northampton - Amherst

Hampton Inn West Springfield

Hotels in Chester with star rating

Frequently asked questions

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