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In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
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26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Cottages in Chesterfield

The Clearing - Quiet - Close To Nature
Exterior

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (202)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
The Clearing - Quiet - Close To Nature
Charming historic cottage on scenic road to Mt. Greylock
Exterior

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (115)
"What a lovely property! And Rich was just terrific!"
Charming historic cottage on scenic road to Mt. Greylock
Massachusetts Vacation Rental w/ Deck
Outdoor dining

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Private Island - Largest Fresh Water Reservoir in Mass
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Westfield Vacation Rental w/ Porch, Pets Welcome!
House (3 Bedrooms) | Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Historic Huntington Home - Walk to Westfield River
House (3 Bedrooms) | Front of property

Historic Huntington Home - Walk to Westfield River

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."
Historic Huntington Home - Walk to Westfield River
Charlemont Retreat on Chickley River w/ EV Charger
House (4 Bedrooms) | 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
Entire cottage in Berkshire Villiage
Exterior

Entire cottage in Berkshire Villiage

3.0 star property
9.6 out of 10, Exceptional, (7)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Cavalier Cottage B&B
Exterior

Cavalier Cottage B&B

3.0 star property
9.0 out of 10, Wonderful, (2)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
Cavalier Cottage B&B
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Outdoor dining

Private Lake Cottage on 3 acres w/350 sq. ft. deck

10.0 out of 10, Exceptional, (1)
"We spent a lovely, relaxing weekend in this well kept and well situated property. Hoping to come back again."
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
House (1 Bedroom) | Front of property

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
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
House (2 Bedrooms) | Interior

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

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
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!
Picturesque Cottage With Sunroom on Ashmere Lake!
Cottage (3 Bedrooms) | Interior

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Cozy Becket Cottage Escape w/ Lake Access!
Cottage (2 Bedrooms) | Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
House (3 Bedrooms) | Interior

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

3.0 star property
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
Lakefront Westhampton Cabin w/ Beach + Kayaks!
House (3 Bedrooms) | Interior

Lakefront Westhampton Cabin w/ Beach + Kayaks!

3.0 star property
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Historic Farmhouse Near Mountains & Colleges!
House (4 Bedrooms) | Interior

Historic Farmhouse Near Mountains & Colleges!

3.0 star property
Historic Farmhouse Near Mountains & Colleges!
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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Top Chesterfield Hotel Reviews

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Good internet, good hot breakfast, nice beds, good water pressure in shower."
Mary 2-night trip
Posted 2 days ago
Comfort Inn & Suites

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