Simsbury Holiday Rentals

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Our top choices for Simsbury holiday rentals

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is AU$947
includes taxes & fees
6 May - 7 May
Newly Renovated 2 floor Getaway

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$473
includes taxes & fees
6 May - 7 May
Big farmhouse in the foothills of the Berkshires

Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
3.0 star property
Windsor
The price is AU$954
includes taxes & fees
18 May - 19 May
Spacious Yard w/ Gazebo: Charming Windsor Retreat

Fully Furnished Private Loft Style Charm Trumbull Elevator

Fully Furnished Private Loft Style Charm Trumbull Elevator
Downtown Hartford
The price is AU$442
includes taxes & fees
1 May - 2 May
Fully Furnished Private Loft Style Charm Trumbull Elevator

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is AU$296
includes taxes & fees
4 May - 5 May
Crested One Place - with Free Parking, Heat & AC

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$448
includes taxes & fees
29 Apr - 30 Apr
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$547
includes taxes & fees
6 May - 7 May
Litchfield Retreat, Wineries, Foliage & Skiing

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (22 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$573
includes taxes & fees
20 May - 21 May
#24 *Serenity* A Lakefront Cottage 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$356
includes taxes & fees
24 May - 25 May
Charming 3 bed/2 bath town home with gorgeous back yard

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$586
includes taxes & fees
29 Apr - 30 Apr
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (38 reviews)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is AU$503
includes taxes & fees
29 Apr - 30 Apr
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

River Overlook - What a view from your deck!

River Overlook - What a 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 AU$422
includes taxes & fees
26 May - 27 May
River Overlook - What a view from your deck!

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (2 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is AU$225
includes taxes & fees
29 Apr - 30 Apr
Humble Abode #2

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 AU$299
includes taxes & fees
12 May - 13 May
Central Chic Pad - with Free Parking, Heat & AC

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$661
includes taxes & fees
26 May - 27 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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, (8 reviews)
"excellent location, cozy apartment"
United States
Monica H.
The price is AU$290
includes taxes & fees
18 May - 19 May
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (13 reviews)
"Amazing stay. Easy check-in/access and Karl was quick to answer any questions I had. The place was immaculate, clean and modern with all the amenities you’ll need. Very convenient and walkable to coffee shops, bars & restaurants. We’ll be back."
United States
Todd L.
The price is AU$421
includes taxes & fees
29 Apr - 30 Apr
Charming Luxury 1BR Near Downtown. Dog Friendly!

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$635
includes taxes & fees
13 May - 14 May
Newly Renovated 4 Bedroom House

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (22 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 AU$253
includes taxes & fees
29 Apr - 30 Apr
Peaceful Meadow Retreat

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, (23 reviews)
"Clean place, simple check in, over great!"
United States
Allison S.
The price is AU$245
includes taxes & fees
3 May - 4 May
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
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

Find out more about Simsbury

Everything you need to know about Simsbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simsbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simsbury holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Simsbury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simsbury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simsbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simsbury holiday rentals we have selected for you start as low as AU$253 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Simsbury rentals

At Expedia, we put the best Simsbury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simsbury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simsbury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simsbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy Lakefront Bungalow w firepit/dock/kayaks: This holiday home rental outside of Simsbury is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Simsbury?

With 4 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 Connecticut Science Center, 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.