A metal bridge with a sign that reads 'Thank You' and a birdhouse on the right.

Holiday Homes in Simsbury

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Simsbury holiday homes

A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

1. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
Sun Filled Lake House Living
A Coca-Cola vending machine and a snack vending machine inside a building.

2. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Windsor Locks
The price is €85
includes taxes & fees
1 Oct - 2 Oct
1 Queen Bed | Micfridge
An outdoor patio with wicker furniture, a glass-top table, and a barbecue grill.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
The price is €149
includes taxes & fees
7 Oct - 8 Oct
Collinsville River Escape / Fall Foliage, Deck & Yard
A patio area with wicker furniture and a brick floor.

4. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The Old Avon 1800 Manor
A patio with a table and chairs, a grill, and a view of a lake.

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

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (72 reviews)
"Wow! What a great place! The house is lovely, very clean, comfy beds and cozy seating. Amazing view and an unbeatable location!"
United States
Kristi M.
The price is €463
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A modern living room with a sofa, a coffee table, and a rug.

6. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is €109
includes taxes & fees
12 Oct - 13 Oct
Entire guest suite in South Windsor, Connecticut
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

7. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (16 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is €262
includes taxes & fees
5 Oct - 6 Oct
The Serene Skyway Retreat
A spacious kitchen with wooden cabinets, a large island, and a dining area with chairs and a rug.

8. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (12 reviews)
"The place is easy to locate. It is as beautiful as the photo. Clean and spacious.I definitely would stay there again."
United States
Delores N.
Spacious Yard w/ Gazebo: Charming Windsor Retreat
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.

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

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Windsor Locks
10.0 out of 10, Exceptional, (11 reviews)
"Great stay, home was comfortable and communication w owner was very smooth!"
United States
Stacey P.
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
A covered patio with a dining table, chairs, and a grill.

10. Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (36 reviews)
"We loved being so close to downtown West Hartford. The house had everything we needed for a fun graduation weekend."
United States
Trish
The price is €544
includes taxes & fees
1 Oct - 2 Oct
Prime West Hartford Center Location: Historic Gem
Dining

11. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (25 reviews)
"Great location and lots of room for grandkids to spread out and fun games for them to play with"
United States
Michael W.
The price is €490
includes taxes & fees
13 Oct - 14 Oct
Prime West Hartford Center: Timeless Charm
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

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

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is €268
includes taxes & fees
1 Oct - 2 Oct
Modern & Cozy Cape | 4 Bedroom House | Central Location
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

13. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
Charming New England Home in West Hartford Center
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

14. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
9.6 out of 10, Exceptional, (9 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is €323
includes taxes & fees
13 Oct - 14 Oct
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A living room with a TV, sofas, armchairs, and a fireplace.

15. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
The price is €407
includes taxes & fees
7 Oct - 8 Oct
Willow Haven 2BR Cozy Retreat, Close to Hartford
A modern dining area with a marble table, white chairs, and a chandelier.

16. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (5 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is €274
includes taxes & fees
4 Oct - 5 Oct
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
A bedroom with a bed, a bedside table, a lamp, and two framed pictures on the wall.

17. Red Door Retreat

Red Door Retreat
Vernon
The price is €256
includes taxes & fees
5 Oct - 6 Oct
Red Door Retreat
A wooden cabin interior with a bench, a rug, and a hanging plant.

18. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is €201
includes taxes & fees
4 Oct - 5 Oct
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

19. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
The price is €274
includes taxes & fees
20 Oct - 21 Oct
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simsbury Hotel Reviews

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"The hotel overall was nice but the pool was very cold"
Nicole 2-night trip
Posted 5 hours ago
Hampton Inn & Suites Hartford/East Hartford

Find out more about Simsbury

Simsbury Holiday Homes information

Number of reviews
273
Accommodation
208 Holiday Homes
Lowest Price
€109
Highest Price
€544