Holiday Homes in Simsbury

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Our top choices for Simsbury holiday homes

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is AU$542
includes taxes & fees
4 May - 5 May
#24 *Serenity* A Lakefront Cottage Retreat

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Relaxing stay"
United States
Kim M.
The price is AU$608
includes taxes & fees
13 May - 14 May
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

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

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (22 reviews)
"Great place"
United States
John S.
The price is AU$446
includes taxes & fees
6 May - 7 May
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is AU$555
includes taxes & fees
3 May - 4 May
Litchfield Retreat, Wineries, Foliage & Skiing

15mins to Hartford, Home in Manchester w/ King Bed

15mins to Hartford, Home in Manchester w/ King Bed
Manchester
9.2 out of 10, Wonderful, (7 reviews)
"Great location, spacious, comfortable and clean. The host was very responsive and easy to work with, Definitely deserves 5 stars for quality and price."
Singapore
Angelo N.
The price is AU$493
includes taxes & fees
13 May - 14 May
15mins to Hartford, Home in Manchester w/ King Bed

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Bloomfield
7.6 out of 10, Good, (4 reviews)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
The price is AU$877
includes taxes & fees
3 May - 4 May
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House
Enfield
10.0 out of 10, Exceptional, (5 reviews)
"The house was perfect for a weekend wedding trip. "
United States
Liane V.
The price is AU$632
includes taxes & fees
13 May - 14 May
Newly Renovated 4 Bedroom House

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (145 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is AU$453
includes taxes & fees
3 May - 4 May
Big farmhouse in the foothills of the Berkshires

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (8 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is AU$424
includes taxes & fees
12 May - 13 May
Modern & Cozy Cape | 4 Bedroom House | Central Location

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, (64 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AU$667
includes taxes & fees
26 May - 27 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is AU$170
includes taxes & fees
6 May - 7 May
Entire guest suite in South Windsor, Connecticut

#27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is AU$722
includes taxes & fees
7 May - 8 May
#27- Luxury Collection

Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway
Forest Park
8.8 out of 10, Excellent, (3 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 AU$451
includes taxes & fees
4 May - 5 May
Newly Beautiful renovated first floor apartment getaway

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (13 reviews)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is AU$401
includes taxes & fees
5 May - 6 May
The Serene Skyway Retreat

Charming 3 bed/2 bath town home with gorgeous back yard

Charming 3 bed/2 bath town home with gorgeous back yard
Forest Park
9.8 out of 10, Exceptional, (13 reviews)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
United States
Barbara W.
The price is AU$358
includes taxes & fees
24 May - 25 May
Charming 3 bed/2 bath town home with gorgeous back yard

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
9.6 out of 10, Exceptional, (5 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is AU$620
includes taxes & fees
13 May - 14 May
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

#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, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is AU$804
includes taxes & fees
11 May - 12 May
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
The price is AU$553
includes taxes & fees
4 May - 5 May
Willow Haven 2BR Cozy Retreat, Close to Hartford

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Bloomfield
9.0 out of 10, Wonderful, (6 reviews)
"I had a great time and I felt very welcome"
United States
Avis b.
The price is AU$977
includes taxes & fees
4 May - 5 May
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

#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.
#26 Beautifully Renovated 2 BR Home
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

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Simsbury Holiday Homes information

Number of reviews
321
Accommodation
223 Holiday Homes
Lowest Price
AU$170
Highest Price
AU$977