Simsbury Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Simsbury vacation rentals

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
$197 nightly
The price is $210
Feb 23 - Feb 24
Total with taxes and fees
Central Chic Pad - 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.
$163 nightly
The price is $184
Feb 9 - Feb 10
Total with taxes and fees
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
$309 nightly
The price is $331
Feb 22 - Feb 23
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
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.
$252 nightly
The price is $285
Feb 11 - Feb 12
Total with taxes and fees
Charming Luxury 1BR Near Downtown. Dog Friendly!
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.
$250 nightly
The price is $283
Feb 9 - Feb 10
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
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.
$153 nightly
The price is $173
Feb 9 - Feb 10
Total with taxes and fees
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.
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.
$265 nightly
The price is $283
Feb 9 - Feb 10
Total with taxes and fees
The Serene Skyway Retreat
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.
$247 nightly
The price is $280
Feb 16 - Feb 17
Total with taxes and fees
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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.
$106 nightly
The price is $119
Feb 9 - Feb 10
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
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.
$164 nightly
The price is $185
Feb 9 - Feb 10
Total with taxes and fees
Peaceful Meadow Retreat
Private kitchen

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
Chicopee
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
$339 nightly
The price is $385
Feb 9 - Feb 10
Total with taxes and fees
Welcoming 3-bedroom house- Gardner home
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.
$227 nightly
The price is $244
Feb 9 - Feb 10
Total with taxes and fees
Premier League Pad - with Free Parking, Heat & AC
Fridge, microwave, oven, stovetop

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (2 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
$448 nightly
The price is $508
Feb 14 - Feb 15
Total with taxes and fees
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Smart TV

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
$196 nightly
The price is $209
Feb 11 - Feb 12
Total with taxes and fees
Crested One Place - with Free Parking, Heat & AC
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
$247 nightly
The price is $268
Feb 13 - Feb 14
Total with taxes and fees
#26 Beautifully Renovated 2 BR Home
Exterior

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Downtown Hartford
9.6 out of 10, Exceptional, (5 reviews)
"Great location. Clean property"
United States
Sue R.
$175 nightly
The price is $198
Feb 9 - Feb 10
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
1 bedroom, iron/ironing board, free WiFi, bed sheets

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
#2 *Beautiful 1 BR Apartment - Central CT*
Exterior detail

Saint James Manor - Sleeps 24 in Style & Comfort with Parking

Saint James Manor - Sleeps 24 in Style & Comfort with Parking
McKnight
10.0 out of 10, Exceptional, (1 review)
"Our team was traveling together, it was great to have plenty of beds and lots of space in close proximity to Springfield College."
United States
Zachary R.
Saint James Manor - Sleeps 24 in Style & Comfort with Parking
Terrace/patio

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1 review)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
$282 nightly
The price is $318
Feb 9 - Feb 10
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
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

MGM Springfield

MGM Springfield

10/10 Excellent
"The room was immaculate and the staff was great. Unfortunately the coffee pot did not work but it was easily found elsewhere in the hotel. We will stay there again!"
Kent 1-night trip
Posted 2 days ago
MGM Springfield

Find out more about Simsbury

Everything you need to know about Simsbury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simsbury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simsbury vacation 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 low season months. For more hustle and bustle, you may prefer to visit Simsbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simsbury rentals

At Expedia, we put the best Simsbury vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Simsbury?

Yes, you can find vacation rentals near top attractions in Simsbury, or you can go with a more secluded option if you're looking for relaxation. Our travelers say Simsbury has a good selection of restaurants. Make sure you have time to check out the forests and riverfront during your trip.

What's the top vacation rental in Simsbury?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation home rental outside of Simsbury offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Simsbury?

With 3 Expedia vacation rentals, you're sure 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 vacation rental in Simsbury like?

Vacation rentals are private properties you can stay in for a couple of days or more in Simsbury. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for families.