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Compare 33 Cottages in Southwick 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
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Main deck

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Vacation Rental | 3BR | 1BA | 900 Sq Ft | Stairs Required

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Lakefront Tranquility/Fishermans Delight
Upper deck view

Lakefront Tranquility/Fishermans Delight

9.8 out of 10, Exceptional, (18)
"The cabin was simple, clean, and cozy. A great place to slow down, and enjoy a simpler lifestyle with a beautiful view of the lake. We hope to return during the summer when we can enjoy the lake fully. "
Lakefront Tranquility/Fishermans Delight
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!
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Room

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
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!
Charming Windsor Home w/ Private Backyard!
Exterior

Charming Windsor Home w/ Private Backyard!

3.0 star property
Charming Windsor Home w/ Private Backyard!
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
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
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 Southwick

Linny's Updated Lakeview Cottage - Cozy & Modern
Exterior

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (55)
"The Lakeview Cottage exceeded expectations! My family was visiting from out of state for our daughters’ Cheer Competition and it was the perfect home away from home. Home was clean, Host was very communicative and accommodating, would definitely book again!"
Linny's Updated Lakeview Cottage - Cozy & Modern
Island Vibes Home
Living area

Island Vibes Home

10.0 out of 10, Exceptional, (10)
"The home was clean and well cared for, and had everything we needed. The location was perfect for every where we wanted to go. We had shopping near by to keep us in groceries, and we had easy access to roads to get us to/from area sites and attractions. The one snow day we had, someone came and cleared the walkways and driveway so we didn't have to, that was a nice surprise, and they even rolled the garbage can out and back on pick up day. "
Island Vibes Home
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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