Simsbury Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Simsbury holiday rentals

Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
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.
The price is HK$1,141
HK$2,587 total
includes taxes & fees
22 Feb - 23 Feb
#24 *Serenity* A Lakefront Cottage Retreat
Interior

New England Tiny Home Experience: Coffee & More!

New England Tiny Home Experience: Coffee & More!
3.0 star property
Main Street Historic District
The price is HK$1,290
HK$2,610 total
includes taxes & fees
17 Feb - 18 Feb
New England Tiny Home Experience: Coffee & More!
Fridge, microwave, stovetop, coffee/tea maker

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
East Windsor
10.0 out of 10, Exceptional, (21 reviews)
"Clean place, simple check in, over great!"
United States
Allison S.
The price is HK$1,041
HK$1,354 total
includes taxes & fees
16 Feb - 17 Feb
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
Smart TV

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is HK$674
HK$1,627 total
includes taxes & fees
16 Feb - 17 Feb
Crested One Place - with Free Parking, Heat & AC
Interior

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (6 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is HK$915
HK$1,523 total
includes taxes & fees
27 Feb - 28 Feb
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Smart TV, computer monitors

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is HK$674
HK$1,627 total
includes taxes & fees
18 Feb - 19 Feb
Central Chic Pad - with Free Parking, Heat & AC
2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is HK$711
HK$2,108 total
includes taxes & fees
15 Feb - 16 Feb
Private Apartment in Berlin
Smart TV

Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay if you need to stay in Manchester. The apartment was so clean and accommodating. The host was very easy to communicate with! I would gladly stay here again!"
United States
Corey J.
The price is HK$881
HK$1,904 total
includes taxes & fees
16 Feb - 17 Feb
Premier League Pad - with Free Parking, Heat & AC
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is HK$1,246
HK$2,668 total
includes taxes & fees
7 Mar - 8 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Smart TV

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 HK$675
HK$933 total
includes taxes & fees
16 Feb - 17 Feb
Entire guest suite in South Windsor, Connecticut
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$938
HK$1,235 total
includes taxes & fees
15 Feb - 16 Feb
Humble Abode #2
Fridge, microwave, stovetop, coffee/tea maker

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (11 reviews)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
The price is HK$528
HK$2,227 total
includes taxes & fees
17 Feb - 18 Feb
Charming Luxury 1BR Near Downtown. Dog Friendly!
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
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$688
HK$2,250 total
includes taxes & fees
18 Feb - 19 Feb
The Serene Skyway Retreat
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (17 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$732
HK$1,447 total
includes taxes & fees
23 Feb - 24 Feb
Peaceful Meadow Retreat
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (5 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 HK$946
HK$2,174 total
includes taxes & fees
2 Mar - 3 Mar
Modern & Cozy Cape | 4 Bedroom House | Central Location
Smart TV

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, (16 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is HK$930
HK$2,187 total
includes taxes & fees
16 Feb - 17 Feb
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
The price is HK$724
HK$2,915 total
includes taxes & fees
16 Feb - 17 Feb
Willow Haven 2BR Cozy Retreat, Close to Hartford
Fridge, microwave, oven, stovetop

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 HK$4,467
HK$5,795 total
includes taxes & fees
15 Feb - 16 Feb
Charming 3 bed/2 bath town home with gorgeous back yard
Property grounds

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
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$1,048
HK$2,091 total
includes taxes & fees
15 Feb - 16 Feb
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

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)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
The price is HK$1,696
HK$4,163 total
includes taxes & fees
15 Feb - 16 Feb
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
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

Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Staff was great, room was cozy. Nice quiet sitting area to relax and have a cup of coffee."
John 1-night trip
Posted 15 hours ago
Simsbury 1820 House

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:

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Frequently asked questions

Can I find holiday rentals in Simsbury?

Yes, there are holiday rentals close to the most popular sights in Simsbury, 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?

PICON COZY: This holiday home rental outside of Simsbury has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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?

Cultural attractions include Performing Arts Center at Simsbury Meadows, whereas Farmington River is a spot to enjoy nature. While here, Rosedale Farms & Vineyards 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.