
House holiday rentals in Simsbury
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Top-rated house rentals in Simsbury
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Popular amenities for house rentals in Simsbury
House rentals with a pool

Casino Wine Down House
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

The Getaway-HOST & Co.
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.

Pool House
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!

Amazing Oasis Private Pool, BBQ, Pool Table.
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!!

Garden Level Suite with Beautiful Pool
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!

Litchfield Modern Farmhouse
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 .

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature
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!

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

NEW: Spacious Quaint & Convenient Hideaway!
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.

Lake house retreat Granby CT
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!

Lake Escape: Lake Cottage Charm, Lake Front, AC
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!

By The River
Peaceful place. It looked like the photos. The communication was clear and quick respond. Easy access

West Hartford Center Gem 2!
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.

Nest&Rest Escape
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.

Prime West Hartford Center Location: Historic Gem
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.

Island Vibes
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

The Silhouette in Hartford
It's a well-furnished, comfortable stay tucked into a very large house. One block from St Francis hospital. Enjoyed my stay. Thank you!

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

Urban Luxury in Central CT w/ free RV parking
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!

Quiet and Cozy Getaway
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!!

Nature lover’s retreat in NWCT, breathtaking views
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!

Charming Home in Litchfield County on a MAIN ROAD!
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.

The little house that could!
I had a great time here in the space, it felt very comfortable and safe.

Spacious & serene house in Berkshires
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
Destinations to explore
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- Yale University
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Quotonset Beach
- Bushnell Park
- Silver Sands Beach
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Clinton Town Beach
- Bayview Beach
- Grove Beach
- Attawan Beach
- Kent Falls State Park
- Wildemere Beach
- Giants Neck Beach
- The Connecticut Golf Club
- Anchor Beach
- Clinton Beach
- Brownstone Adventure Sports Park
- Dinosaur State Park