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

Holiday Homes in Simsbury

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Simsbury holiday homes

Property grounds

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.
The price is €316
includes taxes & fees
6 Sept - 7 Sept
Sun Filled Lake House Living
Interior

2. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is €349
includes taxes & fees
13 Sept - 14 Sept
Linny's - Private Dock - Lake Access - Firepit
Coffee/tea maker, fridge, microwave, oven

3. 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
9.8 out of 10, Exceptional, (10 reviews)
"Super easy effective rental. Everything was clean and meet everyone one of our needs!"
United States
Matthew R.
The price is €389
includes taxes & fees
25 Aug - 26 Aug
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Terrace/patio

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 price is €457
includes taxes & fees
26 Aug - 27 Aug
The Old Avon 1800 Manor
Outdoor dining

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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is €420
includes taxes & fees
17 Aug - 18 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Smart TV, fireplace

6. 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 €313
includes taxes & fees
24 Aug - 25 Aug
The Serene Skyway Retreat
Smart TV

7. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (8 reviews)
"Good location"
United States
Arthur
The price is €121
includes taxes & fees
18 Aug - 19 Aug
Entire guest suite in South Windsor, Connecticut
Dining

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.
The price is €541
includes taxes & fees
6 Sept - 7 Sept
Spacious Yard w/ Gazebo: Charming Windsor Retreat
TV, books

9. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
The price is €483
includes taxes & fees
18 Aug - 19 Aug
The Game House Arcade – West Hartford
Dining

10. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (24 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 €454
includes taxes & fees
14 Sept - 15 Sept
Prime West Hartford Center: Timeless Charm
Outdoor dining

11. Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (34 reviews)
"Everything was perfect! Amazing place to stay."
United States
J
Prime West Hartford Center Location: Historic Gem
Interior

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 €262
includes taxes & fees
31 Aug - 1 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
2 bedrooms, free WiFi, bed sheets

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is €203
includes taxes & fees
24 Aug - 25 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

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

#22- 4 Br 2 Ba house-Central CT
New Britain
#22- 4 Br 2 Ba house-Central CT
Smart TV

15. 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, (28 reviews)
"Was a great stay"
United States
John S.
The price is €281
includes taxes & fees
9 Sept - 10 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
TV, fireplace

16. 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 €349
includes taxes & fees
17 Aug - 18 Aug
Willow Haven 2BR Cozy Retreat, Close to Hartford
Property grounds

17. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is €289
includes taxes & fees
14 Sept - 15 Sept
Big farmhouse in the foothills of the Berkshires
Dining

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

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"House was great for our family stay!"
United States
Kim A.
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
2 bedrooms, iron/ironing board, WiFi, bed sheets

19. 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, (7 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 €311
includes taxes & fees
14 Sept - 15 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Property grounds

20. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (24 reviews)
"It was great "
United States
Rodrigo C.
The price is €318
includes taxes & fees
18 Aug - 19 Aug
#24 *Serenity* A Lakefront Cottage Retreat
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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Top Simsbury Hotel Reviews

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

8/10 Good
"The breakfast menu was mediocre--don't understand why they just can't fry real eggs instead of what looks like "egg product." Appreciated hot coffee available at our 5 am checkout. I didn't like the fact they did not take license plates of guests--never stayed at a hotel where this was practice. with exception of check in and out I had no interaction with front desk staff. Lots of restaurants within walking distance of the hotel. I would stay here again."
Margaret 2-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Find out more about Simsbury

Simsbury Holiday Homes information

Number of reviews
9,286
Accommodation
208 Holiday Homes
Lowest Price
€67
Highest Price
€256