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Compare 31 Cottages in Southampton with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....
Aerial view

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental | Studio | 1BA | 800 Sq Ft | Steps to Enter

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Massachusetts Vacation Rental w/ Deck
Terrace/patio

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Trainmaster's Inn - Caboose
Private kitchen

Trainmaster's Inn - Caboose

9.4 out of 10, Exceptional, (3)
"Husband is a railfan he was at the tracks several times a day"
The price is SAR 563
SAR 1,196 total
includes taxes & fees
1 Dec - 2 Dec
Trainmaster's Inn - Caboose
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Outdoor dining

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

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Historic Huntington Home - Walk to Westfield River
Exterior

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Lakefront Granby Escape w/ Private Dock & Kayaks!
Living area

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Private Lake Cottage on 3 acres w/350 sq. ft. deck
This living room has an oversized sectional with a large fireplace and smart TV.

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

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Lakefront Otis Home w/ Stunning Views & Boats!
Aerial view

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Hadley Hideaway Cottage
Living area

Hadley Hideaway Cottage

10.0 out of 10, Exceptional, (6)
"We will definitely stay here again! Well maintained, brand new appliances, decor was warm and inviting in a quiet location. "
Hadley Hideaway Cottage
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Living area

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

3.0 star property
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Berkshires Cabin 2 Mi to Appalachian Trail!
Exterior

Berkshires Cabin 2 Mi to Appalachian Trail!

3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
Terrace/patio

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

3.0 star property
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
Springfield Vacation Rental: 1 Mi to Downtown
Living area

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
Hadley Vacation Rental 24 Mi to Springfield!
Living area

Hadley Vacation Rental 24 Mi to Springfield!

3.0 star property
Hadley Vacation Rental 24 Mi to Springfield!
East Otis Vacation Rental w/ Private Deck & Bbq!
Exterior

East Otis Vacation Rental w/ Private Deck & Bbq!

3.0 star property
East Otis Vacation Rental w/ Private Deck & Bbq!
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
Living area

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

2.0 star property
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Living area

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

3.0 star property
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Rustic-chic Home w/ Decks: Pool + Lake Access
Living area

Rustic-chic Home w/ Decks: Pool + Lake Access

3.0 star property
Rustic-chic Home w/ Decks: Pool + Lake Access
Lakefront Summer Cottage~Sparkling clean social distancing space
Clean, clear water!

Lakefront Summer Cottage~Sparkling clean social distancing space

10.0 out of 10, Exceptional, (1)
"The hosts are lovely. The lake is clean and inviting--perfect for swimming, canoeing, kayaking, sailing, etc.. Beautiful lawn with shade and sun to relax and enjoy the view. Gorgeous flowers everywhere. Elevation helps beat the heat of the valley, keeping temps comfortable with nice breeze off lake. Fun little towns to visit. Next door to state forest with trails. Easy drive to Nothhampton. Fresh farm stand around the corner. Cottages are simple, clean and well-stocked. As hosts indicate, there...
Lakefront Summer Cottage~Sparkling clean social distancing space
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 Southampton

Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
Cozy apartment located in quiet Williamsburg
Exterior

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is SAR 563
SAR 960 total
includes taxes & fees
27 Dec - 28 Dec
Cozy apartment located in quiet Williamsburg
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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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