House holiday rentals in Simsbury

Find and book unique houses on Airbnb

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Popular amenities for Simsbury house rentals

House rentals with a pool

Superhost
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top Guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Superhost
Home in Wolcott
5 out of 5 average rating, 5 reviews

Amazing Oasis Private Pool, BBQ, Pool Table.

AmandaRating, 5 stars4 days ago
Glenda was friendly and had great communication from Start to Finish. This was a nice location for a family fun weekend. Although the drive is close enough to stores if you need anything (target/stopnshop/bjs etc), the property is in a quiet and safe neighborhood. The yard is a great place to hang out and relax with the fire pit or have fun in the pool. And when the weather was crappy the pool table and hanging out in the basement den was nice. Everything in the house is labeled and easy to find. We enjoyed the space and would definitely recommend. Thanks again! 😊
Top Guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Top Guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 73 reviews

Stunning luxury home with pool

StephanieRating, 5 stars2 weeks ago
Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!
Guest favourite
Home in Middletown
4.93 out of 5 average rating, 42 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars5 months ago
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!
Superhost
Home in Litchfield
4.67 out of 5 average rating, 24 reviews

Litchfield Modern Farmhouse

RafaelaRating, 5 stars2 weeks ago
The house is exactly what we needed and very well located. Near restaurants, in a beautiful neighborhood and privacy. It was clean, with a big pool, a lot of space outside and with all amenities that was described. I liked so much because the house is very illuminated . I want to stay in it again .
Superhost
Home in New Hartford
4.79 out of 5 average rating, 42 reviews

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

ColleenRating, 5 stars2 weeks ago
We had an amazing stay! David was quick to respond with any questions I had and even came out to hook up the propane tank for the heated pool. I saw in previous reviews about the tricky driveway but David’s description of it is perfectly accurate and not any trouble, just a little steep but nothing super tricky to deal with! The house has a beautiful setup and view, very clean and so much space. Even though it was cold and rainy we had the most fun and peaceful stay at this home. The bride of the bachelorette group said she wants to book with David on her own just for another stay/get-a-way! Highly recommend this beautiful space!

Weekly house rentals

Top Guest favourite
Home in Plymouth
4.98 out of 5 average rating, 44 reviews

Don’t miss out on this cozy escape! w/Skatepark

WilRating, 5 stars1 day ago
Shawn created a special place here. Love all the details, especially the skateboards and music room. The hot tub was lovely after a long day of driving, I soaked again in the morning. ColecoVision console in the game room was so nostalgic along with a great selection of other games. I really enjoyed the grounds. Even wandered down to the dam/waterfall. My mother in law, son and wife all had their own space to stretch out. I could easily spend more time here, it is not just a place to lay your head for the night.
Guest favourite
Home in West Hartford
4.89 out of 5 average rating, 87 reviews

Charming home in West Hartford.

HarolynRating, 5 stars1 week ago
Terrific water pressure in shower & windows. Loved the soft cushion mattress .Very clean and welcoming environment . Suggestion : provide a Keurig machine Would like to stay here again in future.
Top Guest favourite
Home in Farmington
5 out of 5 average rating, 62 reviews

Lake Escape: Lake Cottage Charm, Lake Front, AC

PaulRating, 5 stars3 weeks ago
What a wonderful stay! We loved the location - beautiful view of the lake. House is very comfortable, clean, and easy to get to. Tracie and Sean were excellent in communicating everything we needed to know to have an enjoyable stay. We'll be back again with life jackets and fishing poles so we can enjoy some time on the lake!
Top Guest favourite
Home in Torrington
5 out of 5 average rating, 25 reviews

Quiet and Cozy Getaway

KarenRating, 5 stars2 weeks ago
We came in for a bridal shower. I 100% recommended to other out of towners this listing. Wanted to stay a few more days but our schedules wouldnt allow. It is definitely worth the 5 star review!! Will be staying here in the future to visit my sister less then 2 miles away!!
Top Guest favourite
Home in Windsor
5 out of 5 average rating, 40 reviews

By The River

EhiraRating, 5 stars1 month ago
Peaceful place. It looked like the photos. The communication was clear and quick respond. Easy access
Top Guest favourite
Home in West Hartford
5 out of 5 average rating, 74 reviews

Prime West Hartford Center Location: Historic Gem

JillRating, 5 stars1 week ago
Great space! Perfect location in the hart of West Hartford Center and Blue Back Square. The special touches were so thoughtful. Check in and out was easy too!
Guest favourite
Home in Windsor
4.91 out of 5 average rating, 68 reviews

Island Vibes

JodiRating, 5 stars2 weeks ago
This was the perfect home base for our week exploring Connecticut and Massachusetts. It was a quiet location, comfortable and clean space. Close to everything we needed. Would definitely recommend!
Top Guest favourite
Home in Southwick
5 out of 5 average rating, 22 reviews

Peaceful, Modern Cottage, 20 min to BDL, 2BR/1BA

LynnRating, 5 stars5 months ago
Jessi's place was exactly as described. It was cute and cozy and perfect for what we needed. Jessi responded to any questions quickly and was very clear in any and all instructions. The neighborhood was peaceful and the house was very easy to find. We will definitely be staying again!

Private house rentals

Top Guest favourite
Home in Rocky Hill
4.96 out of 5 average rating, 28 reviews

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT

BrentRating, 5 stars3 days ago
I highly recommend staying at the Riverside Blues House. It is in a charming location and a really well thought out property to stay. Liza really put a lot of thought into making the home not only comfortable but also very welcoming. From the moment I walked in the door you can feel the love in every room. The house is extremely clean with plenty of extras that made my stay very enjoyable. Thank you Liza!
Superhost
Home in Hartford
4.74 out of 5 average rating, 50 reviews

The Silhouette in Hartford

FavourRating, 5 stars6 days ago
When you get to the location, you could feel concerned about the area because of the old buildings around, and also when you get to the location you might feel it would not be a good stay, but immediately you open the door to get in you will be amazed 100%. Very clean, organized, smells so good inside. I was very very impressed. It feels just like home, the linens smells so fresh, you can still perceive the fragrance of the laundry detergent just so you know it was newly washed. I ENJOYED my stay.
Top Guest favourite
Home in Newington
5 out of 5 average rating, 42 reviews

Urban Luxury in Central CT w/ free RV parking

DonnaRating, 5 stars2 weeks ago
The home was in a beautiful neighborhood, which made for nice walks, the kids were able to play ball in the yard, the check in directions were clear, we had 2 vehicles with plenty of additional space, the house was squeaky clean, the beds were comfortable and the photos were very accurate. The ping pong table was awesome distraction when it rained. It was easy to get to stores and restaurants. Laser tag, movies, bowling all a short drive. Host was easy to reach, responded quickly and had friendly attitude. We can recommend the “Flying Monkeys” restaurant where we had dinner to live jazz band! Food was great. All in all despite clouds and rain we had a great time visiting with our grandkids!
Superhost
Home in Torrington
4.9 out of 5 average rating, 97 reviews

Charming Home in Litchfield County on a MAIN ROAD!

JulieRating, 5 stars3 weeks ago
Perfect placement, central to our needs. I love the fact my dog didn't have to be in a crate while we were out. I also love that there were laundry and dishwasher pods. Fantastic stay overall.
Superhost
Home in Ellington
4.8 out of 5 average rating, 66 reviews

Cheerful 3 bedroom home with large back yard

Olga MariaRating, 5 stars1 week ago
Mr. Andrew was great! Made sure we didn't go without. On my next trip I would LOVE to come back. I felt right at home.
Superhost
Home in Winsted
4.75 out of 5 average rating, 8 reviews

Spacious & serene house in Berkshires

DominikRating, 5 stars9 months ago
I rented this AirBnB for my bother and sister and their kids to stay at during my father's funeral services. Silvain was very accommodating and quick to respond to any questions I had. The house has 2 separate sections so my siblings and their families had their own sleeping space. The house was very clean and they even had some free amenities as welcome gifts. There was a bathtub that was out-of-order, but I did see it listed as such in the description prior to renting. The backyard has a wonderful firepit section we were able to enjoy. I highly recommend this rental to anyone looking to rent in this area, even if it would be a little out of your way. As soon as I saw the property, I knew my siblings would love it and I no longer had to stress about where my siblings would stay during my father's funeral proceedings. Thank you Silvain and Victoire for helping to make my that process stress free.
Superhost
Home in Agawam
4.82 out of 5 average rating, 28 reviews

Home near Six Flags/ hot tub

MariaRating, 5 stars1 month ago
This home is just what the pictures show. It was a great first experience with Airbnb. Checking in and out was simple. The only thing we noticed is that one of the bathroom’s trash was not thrown out. Other than that, no other issues. The home is very nice and clean. Just an FYI for future renters, the house is in a Main Street but we didn’t mind the minimal traffic noise, mostly at night, since we live in a big city and are used to it. We would stay here again.
Guest favourite
Home in Harwinton
4.96 out of 5 average rating, 72 reviews

Direct Waterfront with Private Beach - Entire Home

SuzanneRating, 5 stars1 month ago
I grew up on lake harwinton and the lake is just as peaceful and wonderful as I remember. The house was a great find. It was totally stocked with everything one could ever need. That includes firewood and fire starter for the fire pit outside. I did not realize that, and brought my own, but what a great touch! Some airbnbs don't provide firewood. All in all, this Airbnb was perfect. Lawrence and Denise communicated everything very clearly and were quick to respond if I had a question.

Quick stats about house rentals in Simsbury

  • Total rentals

    20 properties

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

Destinations to explore

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  4. Capitol Planning Region
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