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Vacation rentals in Chesterfield, MA and nearby

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All 24 Rentals in the Chesterfield Area
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The following rentals are within 25 kilometres of Chesterfield, Hampshire County, Massachusetts.

From
$167
Per Night
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1 / 22
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Hawley, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (5) Make Enquiry
From
$123
Per Night
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1 / 13
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Becket, MA
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (8) Make Enquiry
From
$620
Per Night
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1 / 11
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Shelburne Falls, MA
7 Bedrooms, 3 Bathrooms, Sleeps 14
Booking
Details Reviews (9) Make Enquiry
From
$124
Per Night
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1 / 9
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Conway, MA
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Linens Provided
  • Central Heating
  • Deck
  • Local Guides/Maps
  • Dryer
  • Microwave
  • Air Conditioning
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The House in Pumpkin Hollow Bed and Breakfast is nestled in the foothills of the Berkshires in Conway, Masschusetts. It is surrounded by woods. fields, and other historic homes. Ideally situated 6 miles off Route 9, it is close to Northampton, Deerfield, Brattleboro, Amherst and Shelburne Falls.... View all property information
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4 of 5 stars Reviewed 30 August 2014
I travel once a year to various interesting destinations with a best friend and this year we chose this Bed and Breakfast for its proximity to the Berkshires for hiking as well as...
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From
$1,606
Per Week
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1 / 16
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Becket, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (9) Make Enquiry
Amenities & Details
  • Deck
  • Microwave
  • Parking
  • Air Conditioning
  • Stereo System
  • Grill
  • Satellite TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge... View all property information
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5 of 5 stars Reviewed 17 January 2014
We had a wonderful time in the Berkshires, and this cottage was the central part of our weekend. The house was superb and extra clean, with everything provided. Views were...
5 of 5 stars Reviewed 1 October 2013
Excellent spot for a quiet retreat. Located on a nice pond with just a few neighbors we never even saw or heard. The cottage has all the essentials. Very clean and inviting...
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From
$161
Per Night
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1 / 13
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Conway, MA
2 Bedrooms, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (10) Make Enquiry
Amenities & Details
  • Washer
  • Refrigerator
  • Satellite TV
  • Parking
  • Deck
  • Playground
  • DVD Player
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to our beautiful home in Western Massachusetts! We built this post and beam home 14 years ago, high on a hill, overlooking our pasture with our beloved four-legged farm friends...and yes, we have goats. There are no neighbors in sight, though some are nearby. We are on a quiet rural road,... View all property information
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5 of 5 stars Reviewed 19 January 2015
What a wonderful place to spend a week-end! John and Pixie are so warm and welcoming and very interesting to talk to. Their beautiful home is full of interesting artifacts and...
5 of 5 stars Reviewed 17 November 2014
I don't have words to described my stay in this place. I was looking for peace and quiet and I found them there. Thanks to John and Pixie for making my stay a peaceful one. I was...
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From
$263
Per Night
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1 / 23
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Plainfield
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Details Reviews (16) Make Enquiry
Amenities & Details
  • Dryer
  • Parking
  • Patio
  • Dishwasher
  • Garage
  • Fireplace
  • Washer
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone. We like to define our country... View all property information
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3 of 5 stars Reviewed 25 August 2014
The home and grounds were lovely but need some updating,and a good cleaning. Location was secluded with plenty of forest and hiking trails, and a scenic lake for fishing. The...
5 of 5 stars Reviewed 29 May 2014
We all thoroughly enjoyed our long weekend at this lovely house. It was spacious, well situated, and well equipped. We were sorry our stay was so short, and the time in the...
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From
$143
Per Night
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1 / 35
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Charlemont, MA
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (101) Make Enquiry
Amenities & Details
  • Washer
  • Microwave
  • Dryer
  • Stereo System
  • Air Conditioning
  • Garage
  • Deck
  • Fax
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B’s. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
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5 of 5 stars Reviewed 31 December 2014
My mother, my dog and I spent the weekend following Christmas at the Cavalier Cottage. We all had an amazing time. The B&B is located close to a few state parks, hiking, and a...
5 of 5 stars Reviewed 26 November 2014
Cavalier Cottage is a gem for people and dogs. My family and I were impressed by the amount of detail put into it---- it had everything you can think of- gourmet tea and...
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From
$341
Per Night
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1 / 32
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Becket, MA
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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5 of 5 stars Reviewed 29 August 2014
This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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From
$372
Per Night
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1 / 12
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Washington, MA
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Shingle style, timber frame, passive solar, Berkshie 'Cottage' Built along side of Coles Brook, the manor is a retreat destination any time of the year. The seclusion and tranquility of the custom built home and site are unique and comforting for family gatherings and weekend getaways. View all property information
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From
$620
Per Night
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1 / 18
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Hinsdale, MA
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Grill
  • Dryer
  • Microwave
  • Parking
  • Hot Tub
  • Refrigerator
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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From
$161
Per Night
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1 / 11
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Hinsdale, MA
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Dishwasher
  • TV
  • Parking
  • Ceiling Fans
  • Deck
  • VCR
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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From
$536
Per Night
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1 / 8
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Charlemont, MA
5 Bedrooms, 3 Bathrooms, Sleeps 14
Bookings
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Garage
  • Water Views
  • Refrigerator
  • TV
  • Parking
  • Microwave
  • Central Heating
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
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From
$1,302
Per Week
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1 / 9
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Becket, MA
3 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
You can 'have it all' in the Berkshires! Our cozy contemporary home is less than 30 minutes from all Berkshire cultural and historical attractions, but tucked away in woodsy peace and privacy. Our four acres look out over a large lawn, lovely flower and herb garden, old apple orchard, and trout... View all property information
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From
$279
Per Night
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1 / 12
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Hatfield
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Central Heating
  • Deck
  • Air Conditioning
  • Terrace
  • Porch
  • TV
  • Wi-Fi
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and... View all property information
Make Enquiry
From
$234
Per Night
View Details
1 / 28
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Northampton
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dining Seats (6)
  • Number Of Bedrooms
  • Guest Count
  • Alarm Clock
  • Bradley...
  • Springfield: 32.0 km
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Light, airy, tasteful, contemporary and comfortable 5 room apartment with kitchen, dining room, living room with fireplace, den/study, bedroom with queen size platform bed. Bathroom has claw foot tub for showers or bath. Private garage bay. Keyless apartment entry. Ten minute walk to downtown... View all property information
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From
$633
Per Night
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1 / 27
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Williamsburg
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Washer
  • Ceiling Fans
  • Fireplace
  • Terrace
  • Parking
  • Air Conditioning
  • Deck
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Flower Hill Farm Retreat is housed within a 1790 farmhouse and studio situated on an east facing hillside fifteen minutes west of Northampton, Massachusetts. You can rent the entire retreat or separate apartments. See Rates below in this write up. Rambling organic gardens, fields and forest... View all property information
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From
$186
Per Night
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1 / 6
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Becket, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Dryer
  • Hairdryer
  • VCR
  • TV
  • Satellite TV
  • Microwave
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water... View all property information
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From
$434
Per Night
View Details
1 / 14
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Northampton
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Microwave
  • Safe
  • Refrigerator
  • Dryer
  • Ceiling Fans
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beautiful in-town single family home for weekly or extended rental in Northampton’s tranquil Smith College neighborhood. 3 Bedroom, 1.5 bath. Max 6. Great for walking the home is close to town, easy to find, and on a very nice street in a gorgeous part of town. This New England home has original... View all property information
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From
$434
Per Night
View Details
1 / 16
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Becket, MA
3 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
Details Make Enquiry
Amenities & Details
  • Grill
  • DVD Player
  • Fireplace
  • Microwave
  • Safe
  • TV
  • Parking
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Lovey 3 Bedroom house on 200 acres in the Beautiful Berkshires. Drive in, close the gate and enjoy the privacy, sunny lawn leading to a small private lake for swimming, canoeing, fishing. Fully furnished and stocked with everything you need for a stay with family or friends. New bathrooms and... View all property information
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From
$248
Per Night
View Details
1 / 14
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Hatfield
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • TV
  • Refrigerator
  • Deck
  • Satellite TV
  • Parking
  • Wi-Fi
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and... View all property information
Make Enquiry
From
$217
Per Night
View Details
1 / 12
Payment Protection
Windsor, MA
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
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From
$372
Per Night
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1 / 16
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Becket, MA
3 Bedrooms, 4 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Microwave
  • DVD Player
  • Dryer
  • Refrigerator
  • Fireplace
  • Garage
  • Dishwasher
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
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From
$2,046
Per Week
View Details
1 / 10
Becket, MA
6 Bedrooms, 3 Bathrooms, Sleeps 11
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Grill
  • Garage
  • DVD Player
  • Porch
  • Washer
  • Dryer
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds.... View all property information
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