House holiday rentals in Simsbury

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Popular amenities for house rentals in Simsbury

House rentals with a pool

Guest favourite
Home in Montville
4.92 out of 5 average rating, 272 reviews

Casino Wine Down House

EsperanzaRating, 5 stars5 days ago
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back
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 stars3 weeks 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, 3 reviews

Amazing Oasis Private Pool, BBQ, Pool Table.

MarisaRating, 5 stars2 weeks ago
This house was perfect for my family to stay for the weekend so we could attend a family wedding. Wish the weather was nicer so we could have enjoyed the pool on our down time. But house was perfect!! Soo cute and Glenda responded very fast. She was so helpful! I would highly recommend this place to anyone and everyone!!
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!
Superhost
Home in Litchfield
4.65 out of 5 average rating, 23 reviews

Litchfield Modern Farmhouse

RafaelaRating, 5 stars1 week 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!
Guest favourite
Home in Montville
4.93 out of 5 average rating, 163 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

KacieRating, 5 stars2 weeks ago
We had a great time at AJ's place! The space is very spacious and comfortable, everything was clean, and the backyard was PERFECT for our group. Close to casinos and restaurants. Highly recommend for groups and families!

Weekly house rentals

Superhost
Home in Windsor
4.82 out of 5 average rating, 39 reviews

NEW: Spacious Quaint & Convenient Hideaway!

HeatherRating, 5 stars2 weeks ago
Lynn was great. We had a small issue with the lock on day two but she responded and fixed it in a very timely manner. The house was difficult to see in the dark upon arrival but it was fine once we knew where we were at.
Top guest favourite
Home in Granby
5 out of 5 average rating, 9 reviews

Lake house retreat Granby CT

DanisaRating, 5 stars4 weeks ago
We had a wonderful stay at the Lake House while celebrating a graduation with our family! The home was clean, cozy, and had everything we needed for a comfortable visit. We had an amazing time enjoying the lake on the kayaks! The host was incredibly responsive and helpful throughout our stay, making everything smooth and stress-free. It was the perfect spot to relax, laugh, and make memories!
Top guest favourite
Home in Farmington
5 out of 5 average rating, 62 reviews

Lake Escape: Lake Cottage Charm, Lake Front, AC

PaulRating, 5 stars2 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 Windsor
5 out of 5 average rating, 39 reviews

By The River

EhiraRating, 5 stars3 weeks 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, 15 reviews

West Hartford Center Gem 2!

DavidRating, 5 starstoday
We had a lovely time and are grateful for the wonderful accommodations. Alison really put a lot of thought into her property and it shows. All the USB chargers everywhere, the kitchen had everything one would need, the array of books was so inviting even to non-readers 😆 and the bathrooms were immaculate. And being right across the police station made our kids feel so safe.
Superhost
Home in Enfield
5 out of 5 average rating, 3 reviews

Nest&Rest Escape

DorsenRating, 5 stars5 days ago
My girlfriend and I had a truly lovely stay at this B&B. From the moment we arrived, it was clear the space was maintained with great care—the place was absolutely pristine. The amenities were thoughtful and well-appointed, making the entire stay feel effortless and comfortable. We especially appreciated the privacy of the location—it felt like our own peaceful retreat, tucked away just enough to disconnect while still being accessible. The hosts went above and beyond to accommodate us, even setting aside a beautiful arrangement of flowers for my girlfriend’s birthday. It was a thoughtful gesture that did not go unnoticed. Communication was excellent throughout—responsive, clear, and genuinely warm. Every interaction felt intentional, with attention to detail that made us feel welcome and valued. Highly recommended for couples looking for a quiet, intimate escape with top-tier hospitality.
Top guest favourite
Home in West Hartford
5 out of 5 average rating, 73 reviews

Prime West Hartford Center Location: Historic Gem

RomanRating, 5 stars2 weeks ago
We had a great stay at Mark’s place. The location is spot-on—just a short walk to the center of West Hartford, a surprisingly charming little town. Whole Foods, cafes, restaurants—all five minutes away. The house is spacious, clean, and has a nice, fresh feel to it. What really stood out was Mark’s attention to detail. Everything you might need is there—extra towels, toiletries, laundry stuff, umbrellas, coffee and kitchen supplies. even charging cables neatly set up by each bed. You can tell it’s been thoughtfully put together. the mattresses are amazing. We all slept like rocks.
Guest favourite
Home in Windsor
4.91 out of 5 average rating, 68 reviews

Island Vibes

JodiRating, 5 stars1 week 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!

Private house rentals

Superhost
Home in Hartford
4.73 out of 5 average rating, 49 reviews

The Silhouette in Hartford

MalcolmRating, 5 stars2 weeks ago
It's a well-furnished, comfortable stay tucked into a very large house. One block from St Francis hospital. Enjoyed my stay. Thank you!
Top guest favourite
Home in Plymouth
4.98 out of 5 average rating, 42 reviews

Don’t miss out on this cozy New England escape!

ChristopherRating, 5 starstoday
Would gladly stay here again. Shawn was responsive and the place had everything we needed. Hope to come back to this part of CT again
Top guest favourite
Home in Newington
5 out of 5 average rating, 41 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!
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 Sharon
5 out of 5 average rating, 28 reviews

Nature lover’s retreat in NWCT, breathtaking views

ScottRating, 5 stars5 months ago
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!
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.
Guest favourite
Home in West Hartford
5 out of 5 average rating, 36 reviews

The little house that could!

MaggieRating, 5 stars5 months ago
I had a great time here in the space, it felt very comfortable and safe.
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.

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

  • Wifi availability

    20 properties include access to wifi

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