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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

Interior

1. 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.
Linny's - Private Dock - Lake Access - Firepit
Property grounds

2. 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 HK$832
HK$2,460 total
includes taxes & fees
9 Sept - 10 Sept
Sun Filled Lake House Living
Smart TV, fireplace

3. 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 HK$996
HK$2,700 total
includes taxes & fees
12 Aug - 13 Aug
The Serene Skyway Retreat
Coffee/tea maker, fridge, microwave, oven

4. 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 HK$1,514
HK$3,585 total
includes taxes & fees
31 Aug - 1 Sept
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Terrace/patio

5. 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 HK$1,820
HK$4,170 total
includes taxes & fees
17 Aug - 18 Aug
The Old Avon 1800 Manor
Outdoor dining

6. 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 HK$2,203
HK$3,850 total
includes taxes & fees
24 Aug - 25 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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 HK$791
HK$1,066 total
includes taxes & fees
17 Aug - 18 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)
"Everything was seamless - we enjoyed the location close to downtown hartford and six flags. the listing was clean and accurate and the beds were comfortable."
United States
AJ P.
The price is HK$2,573
HK$5,657 total
includes taxes & fees
4 Sept - 5 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 Game House Arcade – West Hartford
TV, fireplace

10. 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 HK$727
HK$3,114 total
includes taxes & fees
12 Aug - 13 Aug
Willow Haven 2BR Cozy Retreat, Close to Hartford
Interior

11. 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 HK$1,020
HK$2,310 total
includes taxes & fees
31 Aug - 1 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
Coffee/tea maker, fridge, microwave, oven

12. #26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is HK$1,670
HK$2,878 total
includes taxes & fees
21 Aug - 22 Aug
#26 Beautifully Renovated 2 BR Home
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 HK$1,024
HK$1,832 total
includes taxes & fees
24 Aug - 25 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Property grounds

14. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
The price is HK$1,341
HK$2,620 total
includes taxes & fees
24 Aug - 25 Aug
Big farmhouse in the foothills of the Berkshires
2 bedrooms, iron/ironing board, WiFi, bed sheets

15. 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 HK$1,279
HK$2,920 total
includes taxes & fees
9 Sept - 10 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Smart TV, fireplace, video games, books

16. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (45 reviews)
"It was nice stay!"
United States
Lorrie
The price is HK$1,363
HK$2,783 total
includes taxes & fees
12 Aug - 13 Aug
Cozy & Spacious Entire Home in Springfield
Smart TV

17. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.2 out of 10, Wonderful, (5 reviews)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is HK$1,412
HK$2,643 total
includes taxes & fees
12 Aug - 13 Aug
Beautifully Renovated First-Floor Apartment Getaway
Property grounds

18. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is HK$1,670
HK$3,278 total
includes taxes & fees
18 Aug - 19 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Coffee/tea maker, fridge, microwave, oven

19. #16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is HK$2,510
HK$4,816 total
includes taxes & fees
20 Aug - 21 Aug
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Interior

20. #11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
The price is HK$3,097
HK$5,798 total
includes taxes & fees
15 Aug - 16 Aug
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
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

Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

10/10 Excellent
"Clean room clean bathroom you felt safe walkable to different restaurants. The hotel was old, but it was nearly painted and clean and safe and that’s all I need. Had a great price."
William 1-night trip
Posted 1 hour ago
Motel 6 Wethersfield, CT - Hartford

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