Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Compare 54 Cottages in Chester with updated reviews, rates, and availability.

Massachusetts Vacation Rental w/ Deck
Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Charlemont Retreat on Chickley River w/ EV Charger
Interior

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Interior

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Spacious Historic Home in the Berkshires!
TV, fireplace, books

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Stockbridge Home: Walk to Town Beach!
Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
House (2 Bedrooms) | 2 bedrooms, iron/ironing board, bed sheets

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Historic Huntington Home - Walk to Westfield River
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Picturesque Cottage With Sunroom on Ashmere Lake!
Exterior

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Lakefront Otis Home w/ Stunning Views & Boats!
House (2 Bedrooms) | Interior

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Becket Home w/ 3-season Porch: Walk to Lake Access
Interior

Becket Home w/ 3-season Porch: Walk to Lake Access

3.0 star property
Becket Home w/ 3-season Porch: Walk to Lake Access
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Terrace/patio

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

3.0 star property
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Interior

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

3.0 star property
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Property grounds

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
House (2 Bedrooms) | Living area | TV

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Forget-me-not by Avantstay Bold Lakefront Escape
Interior

Forget-me-not by Avantstay Bold Lakefront Escape

3.0 star property
Forget-me-not by Avantstay Bold Lakefront Escape
Walk to Dining: Downtown Lenox Guest House!
Interior

Walk to Dining: Downtown Lenox Guest House!

3.0 star property
Walk to Dining: Downtown Lenox Guest House!
'the Mill River Cabin w/ Fireplace & River View!
House (2 Bedrooms) | Interior

'the Mill River Cabin w/ Fireplace & River View!

3.0 star property
'the Mill River Cabin w/ Fireplace & River View!
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
4 bedrooms, iron/ironing board, bed sheets

Cozy Great Barrington Home ~ 1 Mi to Ski Resort!

3.0 star property
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester

The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is NT$7,293
NT$8,146 total
includes taxes & fees
May 9 - May 10
The Ponds at Foxhollow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.