Chester Vacation Rentals from $126: 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.

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Our top choices for Chester vacation rentals

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

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

Sherwood Forest

Frank M.

$352 nightly

Sep 7 - Sep 8

Total with taxes and fees

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

$336 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

3. Berkshire Mountain Lodge

Pittsfield

Robert

$113 nightly

Oct 1 - Oct 2

Total with taxes and fees

A house with a porch, a garden with pink flowers, and a stone wall along the road.

4. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

$312 nightly

Sep 7 - Sep 8

Total with taxes and fees

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

$267 nightly

Sep 13 - Sep 14

Total with taxes and fees

A bedroom with a bed, a window, a shelf with books, and a mirror.

6. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Otis

$306 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Anonymous traveler

$402 nightly

Sep 7 - Sep 8

Total with taxes and fees

A cozy room with two beds, large windows, and a view of a snowy landscape.

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

Easthampton Ma.

Paula

$252 nightly

Sep 14 - Sep 15

Total with taxes and fees

A garden area with potted plants, a wooden fence, and outdoor furniture.

9. Cozy Camper tucked into the woods

Sandisfield

$208 nightly

Sep 14 - Sep 15

Total with taxes and fees

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

10. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

$546 nightly

Sep 21 - Sep 22

Total with taxes and fees

A modern two-story house with large windows and a balcony.

11. Cozy Valley View Post & Beam Villa!

Whately

Sharon C.

$960 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

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

Dalton

Elizabeth G.

$290 nightly

Sep 10 - Sep 11

Total with taxes and fees

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

13. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Holyoke

$213 nightly

Sep 7 - Sep 8

Total with taxes and fees

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

14. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

$270 nightly

Sep 8 - Sep 9

Total with taxes and fees

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

15. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveler

$766 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

16. Button's Modern Luxury Walkup Downtown Northampton

Northampton

AMY

$447 nightly

Sep 7 - Sep 8

Total with taxes and fees

A spacious kitchen with a large island, wooden beams, and pendant lighting.

17. Linny's - Private Dock - Lake Access - Firepit

West Suffield

Wendy C.

$355 nightly

Sep 13 - Sep 14

Total with taxes and fees

A bedroom with a bed, curtains, a bedside table, and a lamp.

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

Chicopee

Nicholas B.

$433 nightly

Sep 15 - Sep 16

Total with taxes and fees

A living room with a sofa set, a coffee table, and two lamps.

19. Cozy First Floor Apartment. Located in a quiet neighborhood.

Chicopee

Morrris

$272 nightly

Sep 13 - Sep 14

Total with taxes and fees

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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."

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!"

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Becket Land Trust Historic Quarry. Chester Town Hall and Jacob's Pillow 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.

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Check prices for these dates

Our top choices for Chester vacation rentals

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

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

3. Berkshire Mountain Lodge

4. Big farmhouse in the foothills of the Berkshires

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

6. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

7. Charming, updated 3 bedroom farmhouse farm stay.

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

9. Cozy Camper tucked into the woods

10. Treetop Hideaway in Tyringham

11. Cozy Valley View Post & Beam Villa!

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

13. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

14. Riverside Retreat in the Berkshires

15. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

16. Button's Modern Luxury Walkup Downtown Northampton

17. Linny's - Private Dock - Lake Access - Firepit

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

19. Cozy First Floor Apartment. Located in a quiet neighborhood.

Find vacation rentals that suit your style

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

Find out more about Chester

Frequently asked questions

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