House vacation rentals in Simsbury

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Popular amenities for Simsbury house rentals

House rentals with a pool

Guest favorite
A saltwater pool features a vibrant blue surface and is surrounded by a spacious terrace. Sun loungers are positioned along the poolside, and a fenced area provides safety. Lush greenery creates a serene backdrop, enhancing the outdoor space for relaxation.
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars7 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
Superhost
Home in Egremont
5 out of 5 average rating, 4 reviews

Exquisite family friendly home with heated pool!

AmyRating, 5 stars9 months ago
We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.
Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars7 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 favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Guest favorite
A spacious outdoor area is visible, featuring a winding path that leads through a grassy landscape. Trees of varying heights frame the view, capturing seasonal colors with a backdrop of rolling hills under a clear blue sky.
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries
Guest favorite
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Superhost
A rural scene features a charming two-story building with a mix of red and natural wood exteriors. A stone wall and wooden fence line a pathway leading toward the structure, surrounded by greenery and autumn foliage under a cloudy sky.
Home in Roxbury
5 out of 5 average rating, 22 reviews

Zoom Map 5* Town Roxbury! "Tophet Pool" PoshPadsCT

AllanRating, 5 stars19 months ago
Beautiful home, exactly how it was described and looked even better in person. Incredible surrounding areas and activities. Steven was helpful throughout the stay and incredibly flexible. Wonderful host! Will definitely be planning a yearly visit.
Top guest favorite
A neutral-toned hallway with warm wooden flooring is shown, leading to a sunlit space at the end. A stylish chair is positioned near a floor-to-ceiling window, allowing natural light to fill the area. Multiple doors line the sides of the hallway.
Home in Roxbury
5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars2 months ago
My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.

Weekly house rentals

Guest favorite
Large windows frame a tranquil view of Candlewood Lake, with greenery visible in the foreground. Soft light filters through the trees, creating a serene atmosphere. A wooden table is set beside the windows, enhancing the connection to the outdoors.
Home in Brookfield
4.82 out of 5 average rating, 22 reviews

Lake Candlewood Retreat

FabioRating, 5 stars4 months ago
Nice place .. host is very responsive and helpful and place is nice .. beautiful lake views .. spent 30 days while renovating my house Nd was a smooth stay..
Top guest favorite
Home in Egremont
4.98 out of 5 average rating, 135 reviews

A sunny, quiet chalet beautifully decorated.

SueRating, 5 stars2 months ago
Beautiful, clean and great location! We were up skiing at Catamount so the location was ideal, and the sauna was a nice treat everyday. The house is beautifully decorated and spacious and open. There are a few different levels so plenty of room to spread around with a separate spacious TV/exercise/bunk room in one of the levels. The 2 king beds and twin beds in the bedrooms were all very comfortable and each of the bedroom had their own bathroom next door. The kitchen is fully stocked with kitchenware and necessities/spices etc. Kids went sledding and we even hiked up several times to the top of the hill with great views. Carolyn was very responsive and accommodating.
Guest favorite
Home in Tolland
4.95 out of 5 average rating, 56 reviews

Spacious Home w/ Hot Tub in Private Lake Community

AuraRating, 5 stars1 week ago
The place was incredibly beautiful. The photos did not do it justice. It is in the middle of nowhere. Tina was very detailed in her instruction and one of them was that you must bring groceries because the closest grocery store is 30 minutes away. If you decide to book this place, read her detailed instructions. They are very helpful. The home offered a full kitchen which made it so easy for us to prepared our family's meals without struggling. The hot tub was such a treat. The basement had lots of games, a couch to launch and another TV. Perfect if you come with children. We were seven adults and we did not feel that we where on top of each other. The high ceiling truly made one of our boys (the giant) feel at home. Even the basement had a high ceiling. Pretty cool. Tina was incredibly nice and flexible. Check in is at 4 pm and we arrived earlier. We decided to contact her to see if it would be okay to check in earlier and she accommodated us. Thank you soooo much.
Guest favorite
A two-story house features light yellow siding with blue shutters around the windows. The front yard is well-maintained, showcasing green grass and neatly trimmed bushes on either side of the entrance. A concrete driveway runs alongside the home.
Home in Enfield
4.91 out of 5 average rating, 11 reviews

3 bdrm house great neighborhood

J DavidRating, 5 stars11 months ago
Wonderful place for our family to spend the weekend while we attended our daughter's graduation a half hour away in MA. Clean, comfortable, spacious and charming in a quiet neighborhood. Auria provided clear instructions, check in was a breeze, and she was extremely proactive and helpful. She responded immediately to questions and was always cheerful and polite. One of the best Airbnb experiences we have had so far. I can not recommend this highly enough.
Guest favorite
A bright bedroom is presented with a spacious bed, accented by a light-colored comforter. A wooden dresser and a bedside lamp add to the decor. Natural light streams through two windows with light curtains, providing a serene atmosphere.
Home in New Britain
4.89 out of 5 average rating, 104 reviews

5•Star CapeCodStyle Gem with Bedroom on the Main

ErikaRating, 5 stars1 week ago
We had a short stay at Chanaā€˜s place, but everything was perfect for our family. We will definitely book again and recommend to others. Thank you Chana.
Guest favorite
A rustic cottage is nestled among vibrant green trees, surrounded by a spacious lawn. A large deck extends from the cottage, offering a quiet retreat. The scene captures the tranquility of nature, with dappled sunlight filtering through the leaves.
Home in Sharon
4.92 out of 5 average rating, 150 reviews

Cottage In Nature w/Private River Access

FaithRating, 5 stars2 months ago
We enjoyed a lovely snowy weekend hiking, eating at local restaurants and curling up by the fire. This looks like a great place to return to during the summer for enjoying the outdoor amenities as well!
Top guest favorite
A two-story brick house features a spacious covered porch adorned with planters and an American flag. The entrance is framed by two white doors and decorative accents. Lush greenery and small statues are placed along the walkway, enhancing the welcoming faƧade.
Home in Holyoke
4.97 out of 5 average rating, 327 reviews

Explore Holyoke from this charming 3 Bedroom house

KimRating, 5 stars2 weeks ago
Everything was perfect! It was a great location for us as we were in town for a Cheer Competition! Joseph met us at the door. Everything was as described and they had everything you could possibly need in case something was forgotten! If we are ever back in the area we will try to stay here again!
Guest favorite
A bright living area features a large flat-screen TV mounted on a white console. Two colorful armchairs and a brown leather couch surround a wooden coffee table, all set on a blue area rug. Light streams in through a window, enhancing the cozy atmosphere.
Home in East Hampton
4.92 out of 5 average rating, 93 reviews

Clean private home near Lake Pocotopaug!

CathyRating, 5 stars3 months ago
I highly recommend this property. It was perfect for our Christmas visit with family. The furniture and beds were very comfortable. We truly enjoyed our stay in East Hampton. We will be back!

Private house rentals

Guest favorite
The exterior of a Victorian house is shown, featuring a distinctive gray shingle facade and multiple gabled roofs. Surrounding greenery, including a bush with red berries, adds color to the scene. A porch with steps can be seen leading to the entrance.
Home in Hartford
4.9 out of 5 average rating, 73 reviews

Renovated & Modern Victorian in Historic West End

JoshuaRating, 5 stars3 weeks ago
I’ve stayed here a few times. I keep coming back because Antonio is a great host. His house is always convenient, clean and comfortable. Can’t really ask for more!
Superhost
The home's exterior displays a well-maintained brick faƧade framed by vibrant shrubbery. A spacious lawn with neatly trimmed grass extends in front, complementing the inviting entryway. A driveway along the side leads to a garage, while trees provide a natural backdrop.
Home in Springfield
4.86 out of 5 average rating, 28 reviews

3 Bedroom Home Quiet Area

CatherineRating, 5 stars2 months ago
Our work crew said that they found Bob's place full of old-world charm while also providing all the modern necessities. If you're looking for a hip TikTok hang, this may not be the place for you, but if what you want is a clean, comfortable home for relaxing or remote work, Bob's place is highly recommended. It was a welcome respite from long workdays. Bob was easy to work with and the photos are an accurate presentation of the space. Bob even made sure the drive and walk areas were snow and ice free during their stay. Thanks Bob!
Guest favorite
A light-filled living area features a sofa adorned with green and textured throw pillows. Two stylish chairs complement a round coffee table, and a large bookshelf showcases a collection of books and decorative items. A vibrant area rug covers the wooden floor.
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars2 months ago
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.
Guest favorite
A cozy sitting area is framed by wooden beams and features a pair of light-colored armchairs. A small area rug is placed on the light wood floor, while a ladder leads to the lofted space above. A framed image of an animal decorates the wall.
Home in Egremont
4.94 out of 5 average rating, 77 reviews

Modern and Stylish Country Lakeside Cottage

DylanRating, 5 stars2 months ago
fantastic and cozy, nice backyard, well equipped with amenities as well
Guest favorite
A rustic red wooden cabin is set against a backdrop of lush green trees. The structure features a sloped roof and a welcoming front porch with steps leading up to it. The surrounding area includes gravel pathways and picnic tables for outdoor gatherings.
Home in Colebrook
4.96 out of 5 average rating, 74 reviews

Log Cabin sleeps 30 bunk style on 350 acres

RomaricRating, 5 stars7 months ago
Beautiful time, we can't wait to come again.
Guest favorite
The exterior view of the house features a two-level deck with seating areas, surrounded by a green lawn and bordered by trees. The cozy building is complemented by a chimney, creating an inviting outdoor space that connects with nature.
Home in Otis
4.93 out of 5 average rating, 15 reviews

Spacious Lake Front Home

JeanRating, 5 stars4 months ago
Beautiful location in Otis, right on the lake and so peaceful. The house is very spacious and easily accommodated our family ( 7 adults and 2 children). All the windows in the house provided great views of the lake, especially from the deck. Our host Nick was very responsive when we had questions or any concerns. Would be nice to come for a stay during the summer.
Superhost
A modern living area is visible, featuring a light-colored sofa and a round wooden coffee table. Pendant lights hang above a kitchen island, where seating is arranged. Neutral tones with indoor plants enhance the space, while an entry door leads to natural light.
Home in Springfield
5 out of 5 average rating, 8 reviews

VDM Property!

AlinaRating, 5 stars3 months ago
We enjoyed our stay at this property. It was extremely clean! There were basic necessities provided. It also had a cute, fashionable interior design. The shower and bedrooms were nice. We liked the layout of this property. Our only issue was that either the heater in the master bedroom wasn't working, or we couldn't figure out how to use it.
Guest favorite
The white estate is framed by bare trees, showcasing a combination of traditional architecture and natural surroundings. A serene lawn is visible in the foreground, with stone walls adding rustic charm. Soft lighting illuminates the porch, creating a welcoming atmosphere.
Home in East Haddam
5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

AnjaliRating, 5 stars4 months ago
Spent a wonderful Thanksgiving weekend at Travis' place with my husband and two young daughters. The house is beautifully appointed and so cozy. We played games by the fire, watched a movie in the cozy tv room, and made and enjoyed lovely meals in the kitchen. The house is even more magical than it looks in the photos, and we certainly hope to be back.

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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  2. United States
  3. Connecticut
  4. Hartford County
  5. Simsbury
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