Search Cottages in Simsbury

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

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

The Cottage at Highland Lake, year-round, waterfront with a boat dock
Beach nearby, sun loungers, beach towels

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
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (31)
"Stayed here for a work trip for a couple of nights. Very comfortable, quiet, and nice scenery."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Reel Simple on Bolton Lake
Outdoor dining

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!
Fridge, microwave, stovetop, dishwasher

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!
House (3 Bedrooms) | Interior

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

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
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!
House (3 Bedrooms) | Interior

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!
House (2 Bedrooms) | Interior

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Charming Farmhouse w/ Pool & Fishing Pond!
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Modern Terryville Cottage w/ Deck & Lake View!
Cottage (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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
Interior

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
Interior

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.
Living area

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!
Interior

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
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
Waterbury Home: Playground & Porch Swing
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Waterbury Home: Playground & Porch Swing

3.0 star property
Waterbury Home: Playground & Porch Swing
Tolland Cabin w/ Private Hot Tub & Grill!
TV, fireplace, books

Tolland Cabin w/ Private Hot Tub & Grill!

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

Harwinton Cottage

Harwinton Cottage
Camellia Springs - Solace & Rest
Pool

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.
Don't see what you're looking for?
See all available properties in Simsbury
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Simsbury

PICON COZY
Fridge, microwave, oven, stovetop

PICON COZY

7.8 out of 10, Good, (62)
"Peaceful everything just as listed "
The price is SAR 281
SAR 638 total
includes taxes & fees
27 Apr - 28 Apr
PICON COZY
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

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!
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Great location and pleasant area to walk to area restaurants and shops. Prompt and friendly communication with host who was very accommodating to our needs. We enjoyed our stay."
The price is SAR 469
SAR 1,473 total
includes taxes & fees
27 Apr - 28 Apr
Blue Back Bungalow
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.