Simsbury Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Simsbury holiday rentals

Property grounds

Holiday Home in Middletown

#24 *Serenity* A Lakefront Cottage Retreat
9.8 out of 10, Exceptional, (21 reviews)
"It was our 3rd time staying and everything was as expected. New updates to the bathroom were nice surprise. Thanks again for a lovely stay while we visited our daughter at Wesleyan. "
United States
Robb F.
#24 *Serenity* A Lakefront Cottage Retreat
Smart TV

Apartment in Manchester

Crested One Place - with Free Parking, Heat & AC
The price is HK$675
HK$1,621 total
includes taxes & fees
16 Mar - 17 Mar
Crested One Place - with Free Parking, Heat & AC
Desk, iron/ironing board, WiFi, bed sheets

Holiday Home in Berlin

1 Min to I-91 - Newly Renovated Modern 2 BR Home
The price is HK$1,150
HK$2,340 total
includes taxes & fees
24 Mar - 25 Mar
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Property grounds

Apartment in Granby

Peaceful Meadow Retreat
10.0 out of 10, Exceptional, (18 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is HK$662
HK$1,368 total
includes taxes & fees
24 Mar - 25 Mar
Peaceful Meadow Retreat
Interior

Apartment in Manchester Center

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
10.0 out of 10, Exceptional, (7 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is HK$939
HK$1,551 total
includes taxes & fees
17 Mar - 18 Mar
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Property grounds

Apartment in Manchester Center

Humble Abode #2
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$939
HK$1,236 total
includes taxes & fees
15 Mar - 16 Mar
Humble Abode #2
Property grounds

Holiday Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is HK$1,409
HK$2,630 total
includes taxes & fees
26 Mar - 27 Mar
Big farmhouse in the foothills of the Berkshires
Private kitchen

Holiday Home in Torrington

Litchfield Retreat, Wineries, Foliage & Skiing
The price is HK$2,042
HK$3,135 total
includes taxes & fees
16 Mar - 17 Mar
Litchfield Retreat, Wineries, Foliage & Skiing
Interior

Apartment in Torrington

Pristine, Walkable downtown, Entire 2 Bedroom apartment
10.0 out of 10, Exceptional, (17 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is HK$1,252
HK$2,199 total
includes taxes & fees
15 Mar - 16 Mar
Pristine, Walkable downtown, Entire 2 Bedroom apartment
Living area

Holiday Home in Vernon

Luxe Lady Executive & Family Retreat | 1 Bedroom Townhouse
The price is HK$939
HK$1,823 total
includes taxes & fees
15 Mar - 16 Mar
Luxe Lady Executive & Family Retreat | 1 Bedroom Townhouse
Fridge, microwave, oven, stovetop

Apartment in Agawam

Cozy 2-bedroom apartment with movie theater.
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,401
HK$2,273 total
includes taxes & fees
16 Mar - 17 Mar
Cozy 2-bedroom apartment with movie theater.
Smart TV, fireplace

Holiday Home in Windsor Locks

The Serene Skyway Retreat
9.0 out of 10, Wonderful, (12 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 HK$681
HK$2,243 total
includes taxes & fees
16 Mar - 17 Mar
The Serene Skyway Retreat
Smart TV

Holiday Home in Manchester

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
9.6 out of 10, Exceptional, (20 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is HK$931
HK$2,190 total
includes taxes & fees
18 Mar - 19 Mar
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Property grounds

Apartment in Collinsville

River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is HK$1,166
HK$2,258 total
includes taxes & fees
29 Mar - 30 Mar
River Overlook - Check the view from your deck!
WiFi, bed sheets

Apartment in Downtown Hartford

Totally Private Cozy studio in awesome Hartford with WiFi, AC
8.6 out of 10, Excellent, (11 reviews)
"Great location, very nice and clean. "
United States
Manuel M.
The price is HK$1,056
HK$2,154 total
includes taxes & fees
13 Mar - 14 Mar
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Smart TV

Holiday Home in South Windsor

Entire guest suite in South Windsor, Connecticut
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 HK$676
HK$934 total
includes taxes & fees
16 Mar - 17 Mar
Entire guest suite in South Windsor, Connecticut
Living area

Apartment in Downtown Hartford

Fully Furnished Private Loft Style Charm Trumbull Elevator
The price is HK$1,244
HK$2,243 total
includes taxes & fees
13 Mar - 14 Mar
Fully Furnished Private Loft Style Charm Trumbull Elevator
Fridge, microwave, oven, stovetop

Holiday Home in Southington

#27- Luxury Collection
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 HK$1,401
HK$3,332 total
includes taxes & fees
19 Mar - 20 Mar
#27- Luxury Collection
TV, fireplace

Holiday Home in Manchester

Willow Haven 2BR Cozy Retreat, Close to Hartford
The price is HK$810
HK$3,163 total
includes taxes & fees
16 Mar - 17 Mar
Willow Haven 2BR Cozy Retreat, Close to Hartford
Microwave, oven, stovetop, dishwasher

Holiday Home in Rocky Hill

One private bedroom with work space and shared home with spa.
The price is HK$810
HK$1,178 total
includes taxes & fees
14 Mar - 15 Mar
One private bedroom with work space and shared home with spa.
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"We had a last minute change of plans due to weather- Candlewood was an exceptional choice! We will definitely book there again - clean, services were timely...perfect!"
Kimberly 1-night trip
Posted 12 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Simsbury

Search for holiday rentals in Simsbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Simsbury using one of the methods below:

  • View our selection of featured holiday rentals in Simsbury
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  • Enter your travel dates to view the best deals on holiday rentals in Simsbury while they last

Look no further and take a look at our great range of rental properties in Simsbury!

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Frequently asked questions

Can I find holiday rentals in Simsbury?

Yes, there are holiday rentals in Simsbury close to Performing Arts Center at Simsbury Meadows, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Simsbury has a good selection of restaurants. Make sure you have time to check out the forests and riverfront during your trip.

What are some of the best holiday rentals that Simsbury has to offer?

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford: This holiday home rental outside of Simsbury has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Simsbury?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Simsbury stay.

What’s there to see and do in Simsbury?

Explore the area and family-friendly sights such as The Children's Museum, or get out into nature at a spot like Farmington River. While here, Performing Arts Center at Simsbury Meadows and Talcott Mountain State Park are other places worth a visit.

What’s a holiday rental in Simsbury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simsbury. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.