Simsbury Vacation Rentals

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In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Simsbury

Exterior detail
5 Min.Drive to BDL! Remodeled 4-bedroom Home

5 Min.Drive to BDL! Remodeled 4-bedroom Home

2.0 star property
Windsor Locks
$416 nightly
The price is $472
Nov 17 - Nov 18
Total with taxes and fees
5 Min.Drive to BDL! Remodeled 4-bedroom Home
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Berlin
10.0 out of 10, Exceptional, (1)
"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.
$246 nightly
The price is $278
Nov 17 - Nov 18
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Exterior
The Blue Back Bungalow

The Blue Back Bungalow

2.0 star property
West Hartford
9.4 out of 10, Exceptional, (16)
"Very clean, nicely appointed property. Cozy, nicely appointed and comfortable home to stay in for a family of four. Very nice little touches including cookies, chocolates, coffee/tea and fruit. I would stay here again."
United States
Bea F.
$299 nightly
The price is $317
Nov 17 - Nov 18
Total with taxes and fees
The Blue Back Bungalow
Smart TV
PICON COZY

PICON COZY

Sixteen Acres
7.4 out of 10, Good, (69)
"Peaceful "
United States
tyshawn h.
$151 nightly
The price is $171
Nov 17 - Nov 18
Total with taxes and fees
PICON COZY
Terrace/patio
Peaceful Meadow Retreat

Peaceful Meadow Retreat

2.0 star property
Granby
10.0 out of 10, Exceptional, (16)
" Wonderful property, quiet and clean. Beautiful surroundings!"
United States
Craig M.
$158 nightly
The price is $179
Nov 18 - Nov 19
Total with taxes and fees
Peaceful Meadow Retreat
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

Downtown Hartford
8.4 out of 10, Very Good, (23)
"Very clean and spacious! Loved all the amenities. Room itself was a bit echoey, but nice and quiet."
United States
Kiara
$135 nightly
The price is $152
Dec 1 - Dec 2
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Microwave, electric kettle, cookware/dishes/utensils, paper towels
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)
"The place is well located in the city and clean. “Parking available” does not mean free parking provided by the owner. There is metered street parking and pay parking garages."
United States
Nicholas
$170 nightly
The price is $193
Nov 17 - Nov 18
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Dining
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

Middletown
9.8 out of 10, Exceptional, (20)
"Great stay while our son moved into Wesleyan University. It was a nice alternative to staying at one of the local hotels. Clean and comfortable. We love the deck off the back with serene views of that lake. 5 minute drive to Wesleyan University. Will stay again for sure. "
United States
Allison C.
$280 nightly
The price is $298
Nov 18 - Nov 19
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Torrington
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
$230 nightly
The price is $274
Nov 17 - Nov 18
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior
The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery

Plainville
8.8 out of 10, Excellent, (24)
"Pleasure staying here. "
United States
Jesse H.
$257 nightly
The price is $275
Nov 21 - Nov 22
Total with taxes and fees
The Sun Filled Cozy Creamery
Microwave, oven, stovetop
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Enfield
10.0 out of 10, Exceptional, (2)
"Perfect for work. Everything was very clean. Very close to where we needed to be for work."
United States
Ryan O.
$372 nightly
The price is $421
Nov 18 - Nov 19
Total with taxes and fees
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Fridge, microwave, oven, stovetop
2bd/1ba near downtown- 4 mins to Trinity College

2bd/1ba near downtown- 4 mins to Trinity College

South End
6.0 out of 10, (2)
"Easy check in.Easy check out. Will be booking again whenever looking to visit"
United States
Angel F.
$176 nightly
The price is $199
Nov 19 - Nov 20
Total with taxes and fees
2bd/1ba near downtown- 4 mins to Trinity College
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

New Britain
10.0 out of 10, Exceptional, (7)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
$220 nightly
The price is $248
Nov 18 - Nov 19
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
Bloomfield
9.4 out of 10, Exceptional, (3)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
$530 nightly
The price is $601
Nov 25 - Nov 26
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Smart TV
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

2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (5)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
$159 nightly
The price is $179
Nov 23 - Nov 24
Total with taxes and fees
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Dining
The Serene Skyway Retreat

The Serene Skyway Retreat

Windsor Locks
8.8 out of 10, Excellent, (11)
"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
Nov 19 - Nov 20
Total with taxes and fees
The Serene Skyway Retreat
Fridge, microwave, oven, coffee/tea maker
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

New Britain
7.6 out of 10, Good, (7)
" Not bad for the price "
United States
Audrey L.
$329 nightly
The price is $372
Nov 17 - Nov 18
Total with taxes and fees
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Fridge, microwave, oven, stovetop
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

Downtown Hartford
9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
United States
Anonymous traveler
$218 nightly
The price is $247
Nov 18 - Nov 19
Total with taxes and fees
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"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. "
United States
Stacy B.
$279 nightly
The price is $316
Nov 17 - Nov 18
Total with taxes and fees
Private Apartment in Berlin
Exterior
Cozy Modern Farmhouse Private 2 Bdrm Apartment

Cozy Modern Farmhouse Private 2 Bdrm Apartment

Torrington
10.0 out of 10, Exceptional, (4)
"We were happy to have a clean and comfortable place to stay while in Torrington visiting family. The hotels in town are nasty so this was a great alternative. There is a park across the street and an Office warehouse on the street behind, so it’s quiet at night which was a plus. Inside is definitely as advertised, cozy but not cramped, the furniture and decor is well appointed. We will definitely stay again."
United States
Kelly Grace G.
$264 nightly
The price is $315
Dec 1 - Dec 2
Total with taxes and fees
Cozy Modern Farmhouse Private 2 Bdrm Apartment
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

Quality Inn West Springfield

Quality Inn West Springfield

10/10 Excellent
"Very courteous staff. Comfortable, clean room. Always interesting people travelling through."
Scot 2-night trip
Posted 2 days ago
Quality Inn West 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?

Private Apartment in Berlin: This vacation home rental outside of Simsbury is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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, Talcott Mountain State Park and Stratton Brook 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.