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Compare 29 Cottages in Simsbury with updated reviews, rates, and availability.

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

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (31)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Reel Simple on Bolton Lake

2.0 star property
9.8 out of 10, Exceptional, (22)
"We were a little nervous upon arrival, it was exceptionally cold that day Dec 22nd, 2 deg at night ,and we were afraid it wouldn't heat up. However, between the heat pumps and the electric fireplace, it became toasty! Very convenient, 2 bathrooms great !We would definitely book again !"
Reel Simple on Bolton Lake

Modern Terryville Cottage w/ Deck & Lake View!

9.0 out of 10, Wonderful, (4)
"Accommodated us well. Very clean and cute."
Modern Terryville Cottage w/ Deck & Lake View!

Charming Windsor Home w/ Private Backyard!

3.0 star property
Charming Windsor Home w/ Private Backyard!

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

10.0 out of 10, Exceptional, (43)
"Excellent place with modern decor inside and beautiful view of lake from very nice deck. Will definitely stay again! "
Our Cottage - Small in size, Big in character, On beautiful Highland Lake

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

Lakefront Home, Close to Mt Southington!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful house with great views of the lake. "
Lakefront Home, Close to Mt Southington!

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!

Cozy Litchfield House w/ Fenced-in Yard & Fire Pit

3.0 star property
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit

Wolcott Home w/ Deck: Near Connecticut Attractions

3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions

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

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

Charming Farmington Home ~ 5 Mi to Uconn Health!

3.0 star property
Charming Farmington Home ~ 5 Mi to Uconn Health!

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown

Waterbury Home: Playground & Porch Swing

3.0 star property
Waterbury Home: Playground & Porch Swing

Tolland Cabin w/ Private Hot Tub & Grill!

3.0 star property
Tolland Cabin w/ Private Hot Tub & Grill!

Harwinton Cottage

Harwinton Cottage

Camellia Springs - Solace & Rest

2.0 star property
Camellia Springs - Solace & Rest
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 Simsbury

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is AED 459
AED 1,410 total
includes taxes & fees
4 May - 5 May
Blue Back Bungalow

PICON COZY

7.6 out of 10, Good, (64)
"Picon Cozy was a great place to rest our weary heads. The neighborhood was quiet and the lodging/amenities met our needs very nicely. We'll definitely consider this place for future visits to the Springfield area 😊."
The price is AED 275
AED 625 total
includes taxes & fees
4 May - 5 May
PICON COZY

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (15)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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.