Holiday houses in Simsbury

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Popular amenities for Simsbury holiday rentals

Stay near Simsbury's top sights

Heublein Tower37 locals recommend
Talcott Mountain State Park34 locals recommend
The Shoppes at Farmington Valley18 locals recommend
Millwright's Restaurant and Tavern15 locals recommend
Abigail's Grille and Wine Bar14 locals recommend
Harvest Cafe & Bakery12 locals recommend

Other great holiday rentals in Simsbury

Top Guest favourite
Guesthouse in Southbury
4.93 out of 5 average rating, 319 reviews

Charming 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 reviews

Lake 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 reviews

Spacious 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 reviews

Perfect 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 reviews

Quiet 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 reviews

Casa 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 reviews

Beautiful 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 reviews

The 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

Destinations to explore

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  3. Connecticut
  4. Hartford County
  5. Simsbury