Holiday Homes in Simsbury

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Featured Holiday Homes in Simsbury

136 Raymond · Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (20)
"Immaculate Victorian home wonderfully renovated for modern convenience. Perfect Location; easy on/off Interstate 84. Gracious host who was ultra responsive. Very pleasant stay. "
136 Raymond · Prime West Hartford Center Location: Historic Gem

15mins to Hartford, Home in Manchester w/ King Bed

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very spacious location. Ideal fit for our plans. "
The price is AU$576
includes taxes & fees
19 Dec - 20 Dec
15mins to Hartford, Home in Manchester w/ King Bed

Island Vibes Home

10.0 out of 10, Exceptional, (8)
"Such a perfect space for us. Home was spotless! We had a wedding in Hartford, three bedrooms worked out perfectly two bathrooms everyone had plenty of space. Beautiful kitchen and amenities. We would stay here again in a heartbeat. Wish we could’ve stayed longer"
Island Vibes Home

146 Raymond · Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (10)
"Great old West Hartford home. Very convenient to Center activities for us this weekend. Owner great to deal with. Highly recommended."
146 Raymond · Prime West Hartford Center: Timeless Charm

NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly

10.0 out of 10, Exceptional, (1)
"Great home and nice activities with kids."
The price is AU$641
includes taxes & fees
9 Dec - 10 Dec
NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (1)
"Enjoyed one night in this 3Br property. It was comfortable, secure and easy to locate. Great parking, kitchen, tv and wash/dry facilities. Would recommend."
The price is AU$574
includes taxes & fees
1 Dec - 2 Dec
Beautiful 3BR, Rare Find, Clean & Guest Favorite

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is AU$265
includes taxes & fees
2 Dec - 3 Dec
PICON COZY

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is AU$551
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very good, (8)
"Eunice was great to work with, and the place was fantastic for our family of four going to six flags."
The price is AU$422
includes taxes & fees
9 Dec - 10 Dec
Thomas's Cozy Duplex - Centrally Located

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"The Lakeview Cottage exceeded expectations! My family was visiting from out of state for our daughters’ Cheer Competition and it was the perfect home away from home. Home was clean, Host was very communicative and accommodating, would definitely book again!"
Linny's Updated Lakeview Cottage - Cozy & Modern

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

9.8 out of 10, Exceptional, (62)
"House was clean, completely stocked with everything needed and more, great back yard and gathering areas. Property owner helped right away when we reached out. Would definitely recommend. "
Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

Linny’s Cozy Lakeside Family Friendly Home with dock

9.8 out of 10, Exceptional, (17)
"Welcoming and extremely comfortable. We had a wonderful time. Thank you! "
Linny’s Cozy Lakeside Family Friendly Home with dock

Modern cozy home, pet friendly

10.0 out of 10, Exceptional, (1)
"I wish every spot had a ping pong table. My son and I loved being able to play. As well, such a cool shower! Beautiful open space and just what we needed for a quick overnight. "
The price is AU$491
includes taxes & fees
20 Dec - 21 Dec
Modern cozy home, pet friendly

Stylish & Luxurious 3 BDR Home with Play Station

10.0 out of 10, Exceptional, (5)
"Very clean and modern. Friendly and Professional Property Manager."
Stylish & Luxurious 3 BDR Home with Play Station

Beautiful Luxury 2 Bedroom

Beautiful Luxury 2 Bedroom

Pet-Friendly Farmhouse: Cozy with Large Yard

10.0 out of 10, Exceptional, (1)
"House has lots of room and a super nice screened in porch. Plants everywhere add a nice touch. Large fireplace, all upgraded appliances, big eat in kitchen. Property is on a busier road but backyard although clearly still a kind of cluttered farm setting Is quiet. "
Pet-Friendly Farmhouse: Cozy with Large Yard

The Congamond Cottages: Private Lakefront Cottage

8.4 out of 10, Very good, (5)
"This was the perfect place to stay during the big E. It was very peaceful and helpful during the bustle of the fair. We hope to book again next year."
The Congamond Cottages: Private Lakefront Cottage

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
"The house was spacious and nicely furnished downstairs, and with just a tiny amount of effort it could be quite nice. But the communication appears to all be with robots, so apparently no one is managing it. When we arrived, the downstairs half bath had a dirty, unflushed toilet, no hand towels, and 2 out of the 3 lightbulbs didn't work. In the kitchen, there was a working Keurig with plenty of coffee and tea, which was the one amenity that lived up to the description. However, the ice maker...
The price is AU$571
includes taxes & fees
12 Dec - 13 Dec
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Simsbury

136 Raymond · Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (20)
"Immaculate Victorian home wonderfully renovated for modern convenience. Perfect Location; easy on/off Interstate 84. Gracious host who was ultra responsive. Very pleasant stay. "
136 Raymond · Prime West Hartford Center Location: Historic Gem

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is AU$265
includes taxes & fees
2 Dec - 3 Dec
PICON COZY

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.