
Holiday rentals in Simsbury
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Simsbury
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Simsbury holiday rentals
Stay near Simsbury's top sights
Other great holiday rentals in Simsbury
Top guest favourite

Home in Granby
5 out of 5 average rating, 7 reviewsLake house retreat Granby CT
Top guest favourite

Home in Millerton
4.97 out of 5 average rating, 181 reviewsVacation Home In Millerton
Top guest favourite

Home in Andover
4.98 out of 5 average rating, 56 reviewsSpacious Classic Lakefront Home with jet tub
Guest favourite

Home in Great Barrington
4.96 out of 5 average rating, 26 reviewsPerfect Nature Retreat In Great Barrington
Superhost

Cabin in Lebanon
4.86 out of 5 average rating, 14 reviewsCasa Lago
Top guest favourite

Cabin in Cornwall
5 out of 5 average rating, 48 reviewsBeautiful Cabin in Cornwall CT.
Guest favourite

Home in Otis
4.92 out of 5 average rating, 153 reviewsThe Pinnacle House at Otis Ridge Ski Area!
Guest favourite

Home in New Fairfield
4.95 out of 5 average rating, 79 reviewsThe Lakeside Nook
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
Wifi availability
40 properties include access to wifi
Destinations to explore
- Hudson Valley Holiday rentals
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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