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Our top choices for Simsbury holiday rentals

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is £157
includes taxes & fees
11 May - 12 May
Crested One Place - with Free Parking, Heat & AC

#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 £283
includes taxes & fees
18 May - 19 May
#24 *Serenity* A Lakefront Cottage Retreat

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 £157
includes taxes & fees
12 May - 13 May
Central Chic Pad - with Free Parking, Heat & AC

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 £334
includes taxes & fees
13 May - 14 May
Newly Renovated 4 Bedroom House

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 £310
includes taxes & fees
12 May - 13 May
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Best Outdoors near the Berkshires

Best Outdoors near the Berkshires
Winchester
9.8 out of 10, Exceptional, (16 reviews)
"Great stay and wonderful house. "
United States
Rachel B.
The price is £109
includes taxes & fees
11 May - 12 May
Best Outdoors near the Berkshires

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is £266
includes taxes & fees
11 May - 12 May
Big farmhouse in the foothills of the Berkshires

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 £239
includes taxes & fees
11 May - 12 May
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

#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 £281
includes taxes & fees
11 May - 12 May
#23 *COMFORT & LUXURY* 3 BR/2 BA House

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 £257
includes taxes & fees
12 May - 13 May
15mins to Hartford, Home in Manchester w/ King Bed

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is £291
includes taxes & fees
11 May - 12 May
Litchfield Retreat, Wineries, Foliage & Skiing

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 £182
includes taxes & fees
11 May - 12 May
Premier League Pad - with Free Parking, Heat & AC

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 £223
includes taxes & fees
11 May - 12 May
River Overlook - What a view from your deck!

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
The price is £256
includes taxes & fees
17 May - 18 May
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is £150
includes taxes & fees
11 May - 12 May
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

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, (24 reviews)
"Clean place, simple check in, over great!"
United States
Allison S.
The price is £130
includes taxes & fees
11 May - 12 May
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

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 £119
includes taxes & fees
17 May - 18 May
Humble Abode #2

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 £208
includes taxes & fees
18 May - 19 May
The Serene Skyway Retreat

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, (65 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is £360
includes taxes & fees
11 May - 12 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, (9 reviews)
"excellent location, cozy apartment"
United States
Monica H.
The price is £153
includes taxes & fees
11 May - 12 May
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
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, apart-hotels, 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 favorite 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 depends 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 £239 per night. Entering your travel dates in the search wizard you might find 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?

Beautiful retreat in a lake community to the enjoy the summer season. : This holiday home rental outside of Simsbury is located on a lake, and offers a BBQ, laundry facilities and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.