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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, (30)
"The house, property, and location were perfect for our needs (took my daughter and her friend for a long weekend to celebrate her 13th birthday). Everything was easy to navigate and understand. The house was clean and cozy. The lake was spectacular. Couldn’t have asked for a better experience. "
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)
"This cottage was just as the pics show. Great communication with host prior to visit as well as a "Thank you" This is the perfect spot to relax & recharge from stress. The cottage wraps you in warmth, and charm."
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)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is SAR 469
SAR 1,440 total
includes taxes & fees
29 Apr - 30 Apr
Blue Back Bungalow

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

9.4 out of 10, Exceptional, (15)
"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (13)
"Super nice location/convenient "
The price is SAR 544
SAR 765 total
includes taxes & fees
6 Apr - 7 Apr
Lux Boutique Large Private LOFT Pratt St Hartford
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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