Holiday Homes in Simsbury

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Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Simsbury holiday homes

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 AU$350
includes taxes & fees
16 Nov - 17 Nov
Sun Filled Lake House Living

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.6 out of 10, Exceptional, (4 reviews)
"Cute and cozy home away from home! We loved our stay and all the nice features there were!! Everything was neat and clean and host was super amazing and helpful! We definitely will choose this place again if we’re ever in the area."
United States
Leah H.
The price is AU$186
includes taxes & fees
16 Nov - 17 Nov
Collinsville River Escape / Fall Foliage, Deck & Yard

3. 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 AU$624
includes taxes & fees
17 Nov - 18 Nov
The Old Avon 1800 Manor

4. 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, (76 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AU$666
includes taxes & fees
12 Nov - 13 Nov
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

5. Windsor Retreat | Near Hartford & UConn College

Windsor Retreat | Near Hartford & UConn College
Windsor
9.4 out of 10, Exceptional, (13 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 AU$1,014
includes taxes & fees
16 Nov - 17 Nov
Windsor Retreat | Near Hartford & UConn College

6. Prime West Hartford Center | Timeless Charm

Prime West Hartford Center | Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (27 reviews)
"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."
United States
Alan S.
Prime West Hartford Center | Timeless Charm

7. 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, (12 reviews)
"Great location for our six flags visit (about 15 minutes away)."
United States
Stacey B.
The price is AU$612
includes taxes & fees
15 Nov - 16 Nov
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

8. The Game House Arcade | West Hartford

The Game House Arcade | West Hartford
West Hartford
10.0 out of 10, Exceptional, (2 reviews)
"Great location and well equipped. We will be back"
United States
Mike W.
The price is AU$572
includes taxes & fees
12 Nov - 13 Nov
The Game House Arcade | West Hartford

9. 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
The price is AU$642
includes taxes & fees
12 Nov - 13 Nov
Charming New England Home in West Hartford Center

10. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (18 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is AU$417
includes taxes & fees
30 Nov - 1 Dec
The Serene Skyway Retreat

11. Prime West Hartford Center Location | Historic Gem

Prime West Hartford Center Location | Historic Gem
West Hartford
10.0 out of 10, Exceptional, (37 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 AU$913
includes taxes & fees
16 Nov - 17 Nov
Prime West Hartford Center Location | Historic Gem

12. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (13 reviews)
"Good location"
United States
Arthur
The price is AU$163
includes taxes & fees
17 Nov - 18 Nov
Entire guest suite in South Windsor, Connecticut

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

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (11 reviews)
"Great place"
United States
John S.
The price is AU$423
includes taxes & fees
15 Nov - 16 Nov
Modern & Cozy Cape | 4 Bedroom House | Central Location

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

#22- 4 Br 2 Ba house-Central CT
New Britain
9.0 out of 10, Wonderful, (2 reviews)
"Host was great and responsive and the property was perfect for what we needed."
United States
Hilda C.
#22- 4 Br 2 Ba house-Central CT

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

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"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."
United States
Cindy M.
The price is AU$668
includes taxes & fees
20 Nov - 21 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

16. 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, (5 reviews)
The price is AU$274
includes taxes & fees
16 Nov - 17 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester

17. 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, (31 reviews)
"Was a great stay"
United States
John S.
The price is AU$474
includes taxes & fees
16 Nov - 17 Nov
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

18. Lakefront Property with Scenic View - All Seasons!

Lakefront Property with Scenic View - All Seasons!
Enfield
10.0 out of 10, Exceptional, (2 reviews)
"My family and I stayed in this lovely cottage the night before our son’s graduation from UConn (approx 49 mins from campus). It was very clean, in a quiet neighborhood and perfect for our needs. Communication with the host was great. We look forward to staying here again in the future."
United States
Diana M.
The price is AU$618
includes taxes & fees
16 Nov - 17 Nov
Lakefront Property with Scenic View - All Seasons!

19. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
West Springfield
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Jaimie F.
The price is AU$468
includes taxes & fees
17 Nov - 18 Nov
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

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

Elegant 7BR 2.5Bath Victorian Gem Sleeps 16+
McKnight
10.0 out of 10, Exceptional, (3 reviews)
"Apt was very spacious and welcoming. Kitchen gets really warm when you cook but with ac units in every room the rest of the house is comfortable. Definitely a place to stay. "
United States
ERIC m.
The price is AU$1,747
includes taxes & fees
16 Nov - 17 Nov
Elegant 7BR 2.5Bath Victorian Gem Sleeps 16+
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.

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 city centre.

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

Top reviews in Simsbury