
Holiday houses in Simsbury
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Top-rated holiday rentals in Simsbury
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Simsbury
Top Guest favourite

Guesthouse in Southbury
4.93 out of 5 average rating, 319 reviewsCharming Guest Cottage with Modern Amenities
CarolineRating, 5 stars3 months ago
John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!
Top Guest favourite

Home in Granby
5 out of 5 average rating, 7 reviewsLake house retreat Granby CT
DianeRating, 5 stars2 weeks ago
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!
Top Guest favourite

Home in Andover
4.98 out of 5 average rating, 56 reviewsSpacious Classic Lakefront Home with jet tub
JeffreyRating, 5 stars3 months ago
The house felt like coming home. Everything you need was provided. The location is beautiful as is the surrounding area. We needed proximity to family and this was a perfect spot. All the amenities in the home were available and perfect for a weeklong stay. Thank you for a great stay!
Guest favourite

Home in Great Barrington
4.96 out of 5 average rating, 26 reviewsPerfect Nature Retreat In Great Barrington
TriciaRating, 5 stars4 days ago
Wonderful home, 2 min drive from town. Everything was very cozy and comfortable from the beds to the big cozy couch in the living room. Our family of four and my mother-in-law enjoyed all of the space and amenities like the bbq and big tub in the master. We had a wonderful stay and will be back soon!
Superhost

Apartment in Chester
4.77 out of 5 average rating, 197 reviewsQuiet getaway in the Berkshires
MarkRating, 5 stars2 weeks ago
The place is a large upstairs apartment built into a single family home with a business on the first floor. Very Chester. Comfortable and warm. Everything was and felt clean, no worries there.
Superhost

Cabin in Lebanon
4.86 out of 5 average rating, 14 reviewsCasa Lago
JillianRating, 5 stars7 months ago
I didnt want to leave this little cabin in the woods. It felt rustic but had all the modern amenities you would expect in a home. From the rocking chairs on the porch to the comfy beds, there is nothing I could complain about, even if I tried. Marilyn gave excellent suggestions of places to eat and local current events. We left with fall apples, bellies full of clam chowder, and gigantic smiles!!! We have already started planning our return!
Top Guest favourite

Cabin in Cornwall
5 out of 5 average rating, 48 reviewsBeautiful Cabin in Cornwall CT.
JanRating, 5 stars3 weeks ago
Henry's beautiful home and yard provided the perfect getaway for 5 friends who try to get together at least once a year, coming from 3 different states. The large rooms, clean/fresh bed linens and towels, two full bathrooms and spacious living room adjacent to the kitchen gave us jus t the right setting in which to enjoy each other's company. Breakfast at the kitchen table overlooking the backyard was bright and sunny first thing in the morning. We especially liked the backyard patio, which gets sun all day long. After a cold rainy start to our stay, we were able to enjoy a warm afternoon on the patio - sunshine, blue skies, birds, budding trees and the soothing sound of the water fountain and small pond . We found great restaurants in both Kent and in Litchfield. As an avid gardener, I can just picture Henry's beautiful landscaping when all is in bloom later in the season. Very comfortable place to hang out! We wouldn't hesitate to give others a recommendation for Henry's home.
Guest favourite

Home in Otis
4.92 out of 5 average rating, 153 reviewsThe Pinnacle House at Otis Ridge Ski Area!
AmyRating, 5 stars2 months ago
Welcoming, tidy and clean home. Fully functional and amenable to families with young children. A perfect winter getaway spot given its proximity to Otis Ridge. Extremely easy to ski in and ski out. Mary Kay is a lovely host- extremely responsive, helpful and flexible.
Quick stats about holiday rentals in Simsbury
Total rentals
40 properties
Total number of reviews
2.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
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- Hammonasset Beach
- Yale University
- Soundview Beach
- Rocky Neck State Park Bathing Beach
- Stony Creek Beach
- Sea Bluff Beach
- Limewood Beach
- Catamount Mountain Ski Resort
- Six Flags New England
- Quotonset Beach
- Walnut Public Beach
- Woodmont Beach
- Giants Neck Beach
- TPC River Highlands
- Clinton Town Beach
- Taconic State Park
- Thunder Ridge Ski Area
- Anchor Beach
- Attawan Beach
- Bushnell Park
- Bayview Beach
- Clinton Beach
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation