Simsbury Vacation Home Rentals from CA $96: Search Top Private Vacation Homes for Rent

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Our top choices for Simsbury vacation homes

A lakeside picnic area with a bench, two Adirondack chairs, and a picnic table.

1. Sun Filled Lake House Living

Avon

Joseph C.

CA $357 total

includes taxes & fees

Nov 16 - Nov 17

A stone fire pit with two Adirondack chairs and a wooden bench, surrounded by a white fence and trees.

2. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville

Leah H.

CA $183 total

includes taxes & fees

Nov 16 - Nov 17

A patio area with wicker furniture and a brick floor.

3. The Old Avon 1800 Manor

Avon

Anonymous traveller

CA $592 total

includes taxes & fees

Nov 18 - Nov 19

A two-story house with a garage, a driveway, and a river in the background.

4. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

Mike

CA $664 total

includes taxes & fees

Nov 15 - Nov 16

A garden pathway leading to a white arbor with pink flowers, surrounded by lush greenery and a clear sky.

5. Windsor Retreat | Near Hartford & UConn College

Windsor

Delores N.

CA $999 total

includes taxes & fees

Nov 16 - Nov 17

6. Prime West Hartford Center | Timeless Charm

West Hartford

"This very CLEAN house is in an ideal location ... an easy walk to the Center, even easier to Blueback. The house has all the amenities you could want ... coffee, towels, cords for every kind of device on each side of the bed. The kitchen was full of up-to-date dishes, silverware and cookware. Lots of outdoor seating and yard space for kids to play in. The host was easy to communicate with. We would stay here again on our next visit. Thanks, Mark."

Alan S.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove. There is a dining table with chairs and a coffee maker on the table.

7. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks

Stacey B.

CA $609 total

includes taxes & fees

Nov 15 - Nov 16

A room with a sloped ceiling, exposed brick, and a green wall with neon lights.

8. The Game House Arcade | West Hartford

West Hartford

Mike W.

CA $574 total

includes taxes & fees

Nov 16 - Nov 17

A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

9. Charming New England Home in West Hartford Center

West Hartford

karen

CA $645 total

includes taxes & fees

Nov 16 - Nov 17

A kitchen with a wooden table, white cabinets, a built-in oven, and a window with a view.

10. The Serene Skyway Retreat

Windsor Locks

Michael P.

CA $404 total

includes taxes & fees

Nov 30 - Dec 1

A covered patio with a dining table, chairs, and a grill.

11. Prime West Hartford Center Location | Historic Gem

West Hartford

Trish

CA $851 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with a table and two chairs, surrounded by a white railing.

12. Entire guest suite in South Windsor, Connecticut

South Windsor

Arthur

CA $159 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

13. Modern & Cozy Cape | 4 Bedroom House | Central Location

Manchester Center

John S.

CA $419 total

includes taxes & fees

Nov 15 - Nov 16

A modern living room with a grey sofa, a dining table, and a kitchen in the background.

14. #22- 4 Br 2 Ba house-Central CT

New Britain

Hilda C.

CA $632 total

includes taxes & fees

Nov 15 - Nov 16

A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

15. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Southington

"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."

Cindy M.

CA $667 total

includes taxes & fees

Nov 20 - Nov 21

A wooden cabin interior with a bench, a rug, and a hanging plant.

West Springfield

"Adorable home, set up so cute plus being pet friendly means everything to me when deciding. All was as described and our host had everything you could need and more available to us in the well stocked kitchen and bathroom. Very quiet safe and friendly neighborhood on a dead end street, gated walkway as well as a gated driveway made me feel plenty safe enough to take my dog out at night. Bedrooms were welcoming and set up with pretty fairy lights throughout, all three beds were very comfortable...

Jaimie F.

CA $452 total

includes taxes & fees

Nov 18 - Nov 19

A modern kitchen with white cabinets, a stainless steel stove, and a radiator.

20. Elegant 7BR 2.5Bath Victorian Gem Sleeps 16+

McKnight

ERIC m.

CA $1,783 total

includes taxes & fees

Nov 16 - Nov 17

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Learn more about Simsbury

Nestled along the Farmington River, this historic New England town offers scenic bike trails and vibrant fall foliage. Visit Talcott Mountain State Park for panoramic valley views, then explore charming shops and farm-to-table restaurants downtown.

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