Vacation rentals in Simsbury

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Popular amenities for Simsbury vacation 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 vacation rentals in Simsbury

Guest favorite
Guesthouse in Southbury
4.93 out of 5 average rating, 318 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!
Superhost
Apartment in Great Barrington
4.78 out of 5 average rating, 18 reviews

Writer's retreat: study, books, fireplace (Ecobnb)

MelaRating, 5 stars5 months ago
The location and space were great! I worked remotely during most of my stay and was very comfortable with my set up. The dining table was a perfect desk, with good lighting and wifi! Slept well due to it being so quiet at night. A positive experience overall.
Top guest favorite
Home in Granby
5 out of 5 average rating, 7 reviews

Lake house retreat Granby CT

DianeRating, 5 stars1 week 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 favorite
Home in Andover
4.98 out of 5 average rating, 55 reviews

Spacious Classic Lakefront Home with jet tub

CasimirRating, 5 stars3 months ago
I came here in the dead of winter for a writer's retreat with a fellow writer- AND I WOULD DO IT AGAIN! It was a beautiful and inspiring place to write. Perched on Andover Lake, it was too cold to frolic outside but that was actually liberating. There was a rocking chair-ottoman combo in the master bedroom looking out on the lake and watching it freeze while I worked on some writing was so peaceful and perfect. When I needed to switch it up, there was a writer's desk with the same view and I can not overstate how nice and productive it was to work from it. I am sure in the summer it's a really fun stay (there were kayaks and a dock for swimming) but I actually loved being isolated in such an idyllic place. It's near a few other homes but the road was low traffic enough for a cold weather run around half the lake. Marcie was super helpful with suggestions for places to eat. We didn't actually use the recs - but that only speaks to how nice the house was and how hard it was to leave!
Guest favorite
Cottage in Hebron
4.89 out of 5 average rating, 134 reviews

Welcome to The Holly at Amston Lake

MasonRating, 5 stars2 weeks ago
This place is the perfect getaway location, especially for a quiet relaxing weekend. Great host who was super responsive and flexible with me trying to check in early.
Guest favorite
Home in Great Barrington
4.96 out of 5 average rating, 25 reviews

Perfect Nature Retreat In Great Barrington

ChrisRating, 5 stars1 month ago
Terrific space. Beautiful tree view thru big beautiful windows (especially nice when the snow fell.). An ample space with rooms for every need, each perfectly appointed with appropriate furnishing. All details carefully considered. We loved being there. Cleaning fee was high but the space was worth it.
Top guest favorite
Cabin in Cornwall
5 out of 5 average rating, 47 reviews

Beautiful Cabin in Cornwall CT.

JanRating, 5 stars2 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 favorite
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 vacation 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

  • Wifi availability

    40 properties include access to wifi

Frequently Asked Questions

  • Are there house rentals with a dedicated workspace in Simsbury?

    Yes! Work meets play with ease at over 10 house rentals in Simsbury featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly house rentals in Simsbury?

    Four-legged friends are welcome in Simsbury. Choose from more than 10 house rentals for guests traveling with pets.

  • Do house rentals in Simsbury have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Simsbury. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Simsbury?

    Simsbury has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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  5. Simsbury