Chester 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 Chester

Pet friendly

Apartment

Pool

Condo

Family friendly

Hot tub

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Chester hotels

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

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

1. Quality Inn Lee - Lenox South

Lee

Christine

฿3,330

฿3,719 total

includes taxes & fees

27 Sept - 28 Sept

An outdoor patio with white chairs and tables, a central fire feature, and string lights.

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.

A hotel with a sign reading "D. HOTEL & SUITES" on the facade.

2. D. Hotel Suites & Spa

Holyoke

Kerri

฿4,004

฿4,685 total

includes taxes & fees

9 Sept - 10 Sept

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

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.

A hotel room with two beds, a desk, a chair, a lamp, and a window with a view.

3. Hampton Inn Westfield

Westfield

Mykola

฿3,839

฿4,288 total

includes taxes & fees

7 Oct - 8 Oct

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

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

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

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

Great Barrington

Bruce

฿5,288

฿5,907 total

includes taxes & fees

10 Sept - 11 Sept

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.

An outdoor patio with a table and chairs, surrounded by wooden deck and greenery.

5. Becket Motel

Becket

Paul

฿3,456

฿4,964 total

includes taxes & fees

7 Sept - 8 Sept

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

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

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

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

6. Berkshire Lake Lodge

Lee

mike

฿4,814

฿5,378 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Great Barrington

BJORN

฿4,345

฿4,853 total

includes taxes & fees

15 Sept - 16 Sept

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

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.

A hotel room with a large bed, a chair, a nightstand with a phone, a wall-mounted light, and a window with curtains.

8. Quality Inn Westfield - Springfield

Westfield

Thomas

฿3,330

฿3,719 total

includes taxes & fees

4 Oct - 5 Oct

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 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.

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.

9. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

฿2,960

฿3,306 total

includes taxes & fees

8 Sept - 9 Sept

An indoor swimming pool with blue walls, large windows, and several lounge chairs.

A Hampton Inn hotel with a modern design, featuring a large entrance, a well-lit parking area, and multiple flags.

A snack display with various packaged foods and a microwave.

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

10. Hampton Inn Chicopee/Springfield

Chicopee

Margaret

฿4,284

฿4,861 total

includes taxes & fees

20 Sept - 21 Sept

A hotel room with a bed, bedside tables, a TV, and a window with curtains.

A conference room with multiple tables and chairs, a flat-screen TV on the wall, and a patterned carpet.

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

A hotel bar area with a neon sign reading 'The Paper City,' a selection of glasses on shelves, and a digital screen displaying beverage options.

11. Homewood Suites by Hilton Holyoke-Springfield/North

Holyoke

Andrew

฿4,832

฿5,397 total

includes taxes & fees

4 Oct - 5 Oct

A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

A motel with multiple rooms, a well-maintained lawn, and a stone pathway.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

A hotel room with a bed, a desk, and two wall-mounted lamps.

12. Econo Lodge Lee - Great Barrington

Lee

Anna

฿2,154

฿2,407 total

includes taxes & fees

30 Sept - 1 Oct

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 two beds, a TV, a desk, and a chair.

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.

13. Hotel Northampton

Northampton

steven

฿4,074

฿4,550 total

includes taxes & fees

7 Sept - 8 Sept

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

A lakeside dock with kayaks and a covered boat ramp.

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.

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

Lee

James

฿4,197

฿4,688 total

includes taxes & fees

27 Sept - 28 Sept

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

15. Howard Johnson by Wyndham Lenox

Lenox

irene

฿2,601

฿2,905 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

16. Best Western Springfield West Inn

West Springfield

Luz

฿3,357

฿3,842 total

includes taxes & fees

13 Sept - 14 Sept

A modern lounge area with seating options including sofas, chairs, and a hanging chair. Tables and a counter are also visible.

A modern hotel room with a bed, desk, and chair, a small kitchenette, and a bathroom with a shower and toilet.

A food kiosk with a variety of snacks and beverages, a sign for local items, and a counter with a beverage display.

A modern hotel entrance with a glass door, a visible address number, and a clear pathway leading to the entrance.

17. Tru by Hilton Chicopee Springfield

Chicopee

Leon

฿4,022

฿4,563 total

includes taxes & fees

13 Sept - 14 Sept

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.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and umbrellas.

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

18. Residence Inn Springfield Chicopee

Chicopee

Marta

฿5,568

฿6,317 total

includes taxes & fees

13 Sept - 14 Sept

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

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

19. The Yankee Inn

Lenox

Karen

฿3,818

฿4,265 total

includes taxes & fees

22 Sept - 23 Sept

A restaurant with a glass-enclosed patio, wooden flooring, and green upholstered seating.

A reception desk with a large screen displaying a bicycle wheel and the word "enjoy."

A conference room with two desktop computers, a telephone, and leather chairs.

A hotel room with two beds, a desk, a TV mounted on the wall, and a view of the outdoors.

20. Hampton Inn West Springfield

West Springfield

Matthew

฿3,239

฿3,707 total

includes taxes & fees

10 Sept - 11 Sept

View all properties

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

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 stone bridge over a flowing river with rocks and autumn foliage.

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"

The Whitlock

10/10 Excellent

"The Inn was quaint and conveniently situated in downtown Lenox near shops and restaurants and a short drive to Tanglewood. The virtual check-in worked seamlessly, and a friendly, helpful staff member greeted us at the front desk. Our King Room was clean, comfortable and attractive - perfect for our overnight getaway."

D. Hotel Suites & Spa

8/10 Good

"This is a beautiful spot, along the river just outside the city. It’s close to everything but away from the hustle and bustle so it’s quiet and it feels secluded. The property is a bit dated but the rooms are kept up with more modern decor. It was perfect for our stay, and we’ll definitely be back again."

Tru by Hilton Chicopee Springfield

10/10 Excellent

"Great stay, breakfast was ok, busy week loud neighbor. But great place"

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

10/10 Excellent

"New facility. Everything was exceptionally clean. Fabulous and helpful staff."

Berkshire Mountain Lodge

10/10 Excellent

"We were there for a one night stay after a show at Tanglewood. Being able to check in online in advance was excellent and saved us a lot of time. There were three of us traveling (a couple and a family member) so we requested a suite. It was huge, well appointed and so clean. The cost was incredibly reasonable for the amount of space we had! The king bed in its own bedroom was super comfortable, and the pull out couch did the job. We didn’t use any of the extra amenities, but saw a few families with children. Lots of space to roam and wander, both inside and on the property. It was an easy 15 minute drive to Tanglewood, so the location worked great for us. The only negative comment would be there was no do not disturb tag for the door, so housekeeping arrived an hour before checkout and we had to send them away. We will stay again if we are in the area, highly recommended!"

Candlewood Suites West Springfield by IHG

8/10 Good

"The room is big."

Quality Inn West Springfield

10/10 Excellent

"The was nice and clean and front desk staff was friendly."

The Red Lion Inn

10/10 Excellent

"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."

More cheap stays in Chester

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,044

฿2,283 total

7 Sept - 8 Sept

includes taxes & fees

5.4/10 (892 reviews)

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

฿2,914

฿3,335 total

4 Oct - 5 Oct

includes taxes & fees

7.2/10 Good! (1,017 reviews)

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA

฿3,609

฿4,131 total

5 Oct - 6 Oct

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,818

฿4,265 total

22 Sept - 23 Sept

includes taxes & fees

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

฿4,169

฿4,657 total

4 Oct - 5 Oct

includes taxes & fees

7.2/10 Good! (1,001 reviews)

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

1055 South Street Pittsfield MA

฿4,181

฿4,670 total

10 Sept - 11 Sept

includes taxes & fees

9.2/10 Wonderful! (193 reviews)

Frequently asked questions

What's the best place to stay in Chester?

Quality Inn West Springfield, located 20.6 mi (33.1 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 Berkshire Mountain Lodge. 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 880 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 Becket Land Trust Historic Quarry and Jacob's Pillow 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Chester on Expedia.com

Find hotels in Chester, MA from ฿2,283

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. D. Hotel Suites & Spa

3. Hampton Inn Westfield

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

5. Becket Motel

6. Berkshire Lake Lodge

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

8. Quality Inn Westfield - Springfield

9. Best Western Plus Berkshire Hills Inn & Suites

10. Hampton Inn Chicopee/Springfield

11. Homewood Suites by Hilton Holyoke-Springfield/North

12. Econo Lodge Lee - Great Barrington

13. Hotel Northampton

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

15. Howard Johnson by Wyndham Lenox

16. Best Western Springfield West Inn

17. Tru by Hilton Chicopee Springfield

18. Residence Inn Springfield Chicopee

19. The Yankee Inn

20. Hampton Inn West Springfield

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

The Whitlock

D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

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

Berkshire Mountain Lodge

Candlewood Suites West Springfield by IHG

Quality Inn West Springfield

The Red Lion Inn

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

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

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app