Search Vacation Homes in Simsbury

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Vacation Homes in Simsbury

Bring Your Pet & Visit Springfield: Westfield Home
Relax on the covered porch with a comfortable seating area and beautiful views.

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.0 out of 10, (11)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Relax in style with a comfortable sofa, tufted armchair, and sleek coffee table.

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

9.6 out of 10, Exceptional, (32)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
$277 nightly
The price is $314
Aug 6 - Aug 7
Total includes taxes and fees
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
$344 nightly
The price is $364
Aug 6 - Aug 7
Total includes taxes and fees
Big farmhouse in the foothills of the Berkshires
Cozy Lakefront Bungalow w firepit/dock/kayaks
Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Tranquil Litchfield Connecticut Retreat".
Relax on the covered porch, surrounded by lush greenery, with a comfortable rocking chair waiting.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (15)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
$282 nightly
The price is $320
Aug 10 - Aug 11
Total includes taxes and fees
Tranquil Litchfield Connecticut Retreat".
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Cozy living room with a comfortable sofa, coffee table, and fireplace.

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (23)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Historic Farmhouse Near Mountains & Colleges!
Enjoy cooking in this well-equipped kitchen with an oven and stainless steel range hood.

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (9)
"We loved everything about this home! It fit us perfectly and we would love to rent it again!"
Historic Farmhouse Near Mountains & Colleges!
PICON COZY
Enjoy cooking in this fully equipped kitchen with a microwave, coffee maker, and refrigerator.

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
$143 nightly
The price is $162
Aug 13 - Aug 14
Total includes taxes and fees
PICON COZY
Mountaintop Horse Farm with Heated Pool
Relax by the pool surrounded by lush greenery and a traditional house in the background.

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (31)
"We had the best time with the farm animals, great pool and unbelievable views"
Mountaintop Horse Farm with Heated Pool
Charming Farmhouse w/ Pool & Fishing Pond!
Enjoy cooking in this well-equipped kitchen with a stove, sink, and dishwasher.

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (14)
"Everything about the house and property was exactly as described. We had the best time there with plenty of space to spread out. It was very clean and comfortable. The kids had so much fun exploring and they visited the ice cream shop everyday that it was open.We will definitely stay here again."
Charming Farmhouse w/ Pool & Fishing Pond!
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (57)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
$433 nightly
The price is $491
Aug 10 - Aug 11
Total includes taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (5)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Lake Congamond Cozy Stylish Comfortable House
Enjoy a serene lakeside retreat with a boat dock and tranquil views.

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
10.0 out of 10, Exceptional, (4)
"This cozy cottage was perfect. It was definitely a great lication and close to a lot of stores. The beds were really comfortable too. Thesellerr was super helpfula sn"
Lake Congamond Cozy Stylish Comfortable House
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
10.0 out of 10, Exceptional, (4)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
$380 nightly
The price is $406
Aug 6 - Aug 7
Total includes taxes and fees
Private Apartment in Berlin
#28- *Modern Bungalow*
Relax in this stylish living room with a leather sofa, coffee table, and potted plant.

#28- *Modern Bungalow*

9.0 out of 10, Wonderful, (2)
"This stay was very comfortable and also not too fat from the Convention Center either "
#28- *Modern Bungalow*
Upscaled Quiet Neighborhood- Modern 3 BDRM
Kitchen equipped with stainless steel appliances, white cabinetry, and a granite countertop.

Upscaled Quiet Neighborhood- Modern 3 BDRM

10.0 out of 10, Exceptional, (26)
"Nice place to stay"
Upscaled Quiet Neighborhood- Modern 3 BDRM
County Seat Colonial
Relax in a serene bedroom with a large bed, chandelier, and a view through the window.

County Seat Colonial

10.0 out of 10, Exceptional, (11)
"This was just what we needed. Thank you for a beautiful home, adorable town and so much to do! Perfect weekend for my family!"
County Seat Colonial
#26 Beautifully Renovated 2 BR Home
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, dishwasher, and coffee maker.

#26 Beautifully Renovated 2 BR Home

10.0 out of 10, Exceptional, (2)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
#26 Beautifully Renovated 2 BR Home
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Fridge, microwave, oven, stovetop

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Enjoy cooking in this stylish kitchen with an oven, refrigerator, and microwave, complemented by a sink under a window with an outdoor view.

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

10.0 out of 10, Exceptional, (1)
"Spacious, clean and comfortable home. Nice neighborhood near a nice park and trails . Beds were comfortable, kitchen had the pots and pans we needed for dinner and breakfast. Perfect space for us and our 3 adult boys. "
$295 nightly
The price is $334
Aug 13 - Aug 14
Total includes taxes and fees
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simsbury Hotel Reviews

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"I was very comfortable in this hotel and had everything I needed. The bed was heavenly and I loved that the room was a little apartment. The airport access is phenomenal and the shuttle driver was delightful. All the staff at the hotel were friendly and the place just has a nice vibe. Will definitely stay again next time I fly into Bradley."
Sue 1-night trip
Posted 9 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG