Search Cottages in West Simsbury

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 29 Cottages in West 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
East Otis Vacation Rental w/ Private Deck & BBQ!
Desk, internet, bed sheets

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!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (29)
"Vladimir and Cristina's Plymouth listing is such a great find! It was a great home base for visiting family in the area for the holidays. I don't think I've ever been to a rental that had everything you could possibly need. All this plus an amazing view - we'll be back!"
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
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, (1)
"Beautiful place with all the extras that made it feel like staying at a good friend’s house. "
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!
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.
Cottage is currently rented for the year, and not available until further notice
Interior

Cottage is currently rented for the year, and not available until further notice

9.0 out of 10, Wonderful, (2)
"This is a lovely property in a perfect, serene location. Highly recommend!"
Cottage is currently rented for the year, and not available until further notice
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
Family Home w/ Deck & Grills in Southington!
House (3 Bedrooms) | Interior

Family Home w/ Deck & Grills in Southington!

3.0 star property
Family Home w/ Deck & Grills in Southington!
East Otis Vacation Rental w/ Private Deck & Bbq!
Interior

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!
Interior

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

2.0 star property
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
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
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 West 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 West Simsbury

Lux Boutique Large Private LOFT Pratt St Hartford
Iron/ironing board, WiFi, bed sheets

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (12)
"Super nice location/convenient "
The price is AED 459
AED 665 total
includes taxes & fees
26 Mar - 27 Mar
Lux Boutique Large Private LOFT Pratt St Hartford
Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views
Outdoor spa tub

Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views

10.0 out of 10, Exceptional, (1)
"Beautiful view from the upstairs window. I enjoyed the pellet stove on the cold days."
The price is AED 661
AED 1,216 total
includes taxes & fees
26 Mar - 27 Mar
Cozy Lakefront Cottage - Hot Tub, Game Room & Lake Views
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!
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.

Frequently asked questions

Why book your cottage in West Simsbury with Expedia?
We think that vacays should be a walk in the park, so if you’re on the lookout for cottages in West Simsbury at a competitive price, Expedia delivers. Stick to the budget and pick a thrifty option far away from the city rush, or book a 5-star cottage to pamper your favorite people.
How can I find cheap cottages in West Simsbury?
With Expedia’s user-friendly filter tool, getting your hands on cheap cottages in West Simsbury is easy. To discover properties that’ll make your bank balance smile, narrow down your search by amenities, star rating and budget.