
Vacation rentals in Simsbury
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Charming Guest Cottage with Modern Amenities
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!

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

Lake house retreat Granby CT
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!!!

Spacious Classic Lakefront Home with jet tub
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!

Welcome to The Holly at Amston Lake
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.

Perfect Nature Retreat In Great Barrington
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.

Beautiful Cabin in Cornwall CT.
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.

The Pinnacle House at Otis Ridge Ski Area!
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.
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- Yale University
- Catamount Mountain Ski Resort
- Quotonset Beach
- Six Flags New England
- Giants Neck Beach
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Taconic State Park
- Thunder Ridge Ski Area
- Attawan Beach
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- The Connecticut Golf Club
- Burwells Beach
- Fort Trumbull Beach
- Bayview Beach
- Wildemere Beach
- Barbara Pine Memorial Beach
- Anchor Beach
- Grove Beach
- Hartford Golf Club
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