Chester Vacation Rentals from ￥9,107: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Chester has to offer?

Experience Three Sisters Sanctuary in Goshen, MA : Visitors like this Chester vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

A bridge over a calm river with trees and buildings in the background.

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Our top choices for Chester vacation rentals

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

1. Berkshire Mountain Lodge

Pittsfield

Susan J

￥17,266 total

includes taxes & fees

Dec 6 - Dec 7

A spacious living room with a wooden staircase, a dining area, and a television.

2. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

￥45,186 total

includes taxes & fees

Nov 18 - Nov 19

A triangular-shaped building with a balcony and a wooden picnic table in front.

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Brian C.

￥57,429 total

includes taxes & fees

Nov 15 - Nov 16

A hot tub with a string of lights above it, set against a dark night sky.

4. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

￥60,177 total

includes taxes & fees

Nov 15 - Nov 16

A white porch with two rocking chairs, a door, and a number '205'.

5. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

￥55,264 total

includes taxes & fees

Nov 15 - Nov 16

A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

6. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Kyle R.

￥68,831 total

includes taxes & fees

Nov 16 - Nov 17

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

7. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

￥63,149 total

includes taxes & fees

Dec 8 - Dec 9

A rural property with a wooden barn, a white fence, and a mobile home.

8. Cozy Camper tucked into the woods

Sandisfield

"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...

hannah w.

￥27,840 total

includes taxes & fees

Nov 14 - Nov 15

A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

9. Modern Studio Ideal for Traveling Professionals

Holyoke

Kebreab H.

￥36,051 total

includes taxes & fees

Nov 19 - Nov 20

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

10. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Marcia O.

￥47,776 total

includes taxes & fees

Nov 17 - Nov 18

A hot tub on a wooden deck with snow on the ground and trees in the background.

11. The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.

Paula

￥42,507 total

includes taxes & fees

Nov 18 - Nov 19

A two-story residential building with a sign indicating 'Victory Residence' and the address '1785'.

12. Work, Play & Stay! Apt Near Holyoke Medical Center

Holyoke

Yvonne A.

￥46,079 total

includes taxes & fees

Nov 22 - Nov 23

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a pool table.

13. Townhouse with Pool Table - Renovated w/ King Bed

Chicopee

Nicholas B.

￥67,026 total

includes taxes & fees

Nov 16 - Nov 17

A rustic wooden building with a chimney, surrounded by lush greenery and flowering plants.

14. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

￥96,495 total

includes taxes & fees

Nov 16 - Nov 17

A picnic table in a grassy yard with trees and a fence in the background.

15. A Cozy Berkshire Escape l Close to the Slopes

Great Barrington

Kelly B.

￥47,560 total

includes taxes & fees

Nov 25 - Nov 26

A modern kitchen with a central island, bar stools, and a bicycle.

16. Button's Modern Luxury Walkup Downtown Northampton

Northampton

AMY

￥76,095 total

includes taxes & fees

Nov 17 - Nov 18

17. Modern Studio Ideal for Traveling Professionals

Holyoke

￥37,178 total

includes taxes & fees

Nov 22 - Nov 23

A covered porch with string lights, a ceiling fan, and outdoor seating.

18. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

￥95,211 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a front porch, a concrete walkway, and a well-maintained lawn.

19. Cozy Home in Holyoke with 3 bedrooms

Holyoke

Jennifer S.

￥52,328 total

includes taxes & fees

Dec 13 - Dec 14

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

20. Cozy 2-bedroom apartment in Chicopee

Chicopee

Christopher P.

￥34,285 total

includes taxes & fees

Nov 18 - Nov 19

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Find vacation rentals that suit your style

Top Chester Hotel Reviews

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

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

Fairfield Inn & Suites Springfield Holyoke

Holyoke

10/10 Excellent

This hotel is great! The location is right off the highway, making it convenient to get to many areas quickly, using I91 or Riverdale Rd. Breakfast is good, standard hotel food, but fresh. Hot coffee, tea, cocoa available all day and night in the lobby. The lobby is big and a nice area to sit and visit or to just get out of your room for a while. The mall is down the street, and Cracker Barrel, is behind the hotel, McDonalds, and Dunkin’ Donuts in front off. We stay here every time we are in...

Diane

A room with a television on top of a cabinet, a door, and a shelf with items.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

An outdoor patio area with a circular fire pit surrounded by wicker furniture and a stone fire table.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.

Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

10/10 Excellent

Lauren

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

An outdoor seating area with tables and chairs, a sofa, and a large window with various text and graphics.

Tru by Hilton Chicopee Springfield

Chicopee

10/10 Excellent

Tynisa

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.

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

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

Courtyard by Marriott West Springfield

West Springfield

10/10 Excellent

Michael

Find out more about Chester

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Frequently Asked Questions

Can I find a vacation rental in Chester?

Yes, you can find vacation rentals close to well known sights in Chester, or you can select a more secluded option if you want a relaxing place to stay. Chester is known for its waterfalls and shopping. Make sure you have time to check out the riverfront and restaurants during your trip.

What are some of the best vacation rentals that Chester has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: Visitors like this Chester vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Glendale Falls. Chester Town Hall and Pyramid Lake are a couple of places you'll find in the larger area.

What are vacation rentals like in Chester?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Chester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.

Chester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester vacation rentals

1. Berkshire Mountain Lodge

2. Real Estate: Therapy - Lake, Laundry, Love it

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

4. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

5. Big farmhouse in the foothills of the Berkshires

6. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

7. Charming, updated 3 bedroom farmhouse farm stay.

8. Cozy Camper tucked into the woods

9. Modern Studio Ideal for Traveling Professionals

10. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

11. The Creation Station is a cozy place so make yourself at home.

12. Work, Play & Stay! Apt Near Holyoke Medical Center

13. Townhouse with Pool Table - Renovated w/ King Bed

14. Sun Filled Lenox Retreat - Minutes to Tanglewood!

15. A Cozy Berkshire Escape l Close to the Slopes

16. Button's Modern Luxury Walkup Downtown Northampton

17. Modern Studio Ideal for Traveling Professionals

18. Secluded Family Home in Serene Stockbridge Woods

19. Cozy Home in Holyoke with 3 bedrooms

20. Cozy 2-bedroom apartment in Chicopee

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

Find out more about Chester

Frequently Asked Questions

Can I find a vacation rental in Chester?

What are some of the best vacation rentals that Chester has to offer?

What can I see and do in Chester?

What are vacation rentals like in Chester?