Holiday Homes in Connecticut

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Top Cities in Connecticut

Featured Holiday Homes in Connecticut

Our top choices for Connecticut holiday homes

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"A very comfortable short stay in a convenient location"
Cozy 2 bedroom home located minutes from downtown

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.4 out of 10, Exceptional, (12)
"Perfect place to rest. Excellent service! "
The price is €173
includes taxes & fees
24 Sept - 25 Sept
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at the beautiful house with four cottages for our wedding party, and it was truly an unforgettable experience. From the moment we arrived, the breathtaking views of the sound captivated everyone. The serene waters, rolling hills in the distance, and the quiet, peaceful atmosphere set the perfect tone for a memorable celebration.The house itself was stunning—spacious, yet cozy, with modern amenities that didn’t take away from the charming, rustic feel of...
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (102)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Modern Cape Downtown Mystic

10.0 out of 10, Exceptional, (25)
"Perfect location, great backyard, loved our stay!"
Modern Cape Downtown Mystic

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (58)
"My family and I enjoyed our stay and their hospitality!"
Charming 1870 cape cottage in Litchfield

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."
The price is €448
includes taxes & fees
24 Sept - 25 Sept
McAngel Haven: 5 mins from Yale

Sweet Mystic Retreat

10.0 out of 10, Exceptional, (250)
"The house was very clean, plenty of space and well stocked. Would definitely stay there again"
Sweet Mystic Retreat

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

5 Minute Walk to Downtown Mystic

9.6 out of 10, Exceptional, (95)
"Excellent communication with property manager, great location to walk into Mystic shops"
5 Minute Walk to Downtown Mystic

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (66)
"The house is perfectly located. Quiet area but close to downtown Madison and Guilford and so much the CT shoreline has to offer. "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

8.8 out of 10, Excellent, (22)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Stareway to Heaven Su

10.0 out of 10, Exceptional, (8)
"Beautiful house that offered tremendous comfort and amenities, all modern. "
Stareway to Heaven Su

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (14)
"Solid location and quiet neighborhood good after a long day."
Ranch style living at its best with country garden & patio!

Spacious Home Near Mohegan Sun

2.0 out of 10, (1)
"My stay at this rental was deeply unsettling and unsafe. The apartment itself has a creepy, neglected vibe, and it only got worst. A serious safety issue occured when a teenager in our group fell through a rotted, unstable deck/ a terrifying and completely preventable accident. Even more concerning, the entrance code to our apartment was the same code used for all other units in the building. This made me feel extremely unsafe as anyone from another unit could have accessed ours at any time....
The price is €614
includes taxes & fees
6 Oct - 7 Oct
Spacious Home Near Mohegan Sun

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (154)
"Such a unique home in the lovely town! Much to see and do. We need a longer stay. Thank you. "
The price is €347
includes taxes & fees
7 Oct - 8 Oct
Charming Historic House in Downtown Mystic

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

8.0 out of 10, Very good, (9)
"Affordable, fun, relaxing house. Indoor and outdoor things to do. Some pretty glass decor in the dining room, so I easily moved a few things to temporarily kid proof it. A/C in bedrooms, ceiling fans in almost every room. The hosts were very responsive and addressed our concerns exceptionally well."
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (67)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Cape Cod home in great location! Walk to downtown

9.4 out of 10, Exceptional, (156)
"Great place to stay in a nice location.Enjoyed our vacation here."
Cape Cod home in great location! Walk to downtown
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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Top Connecticut Hotel Reviews

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Find out more about Connecticut

Connecticut Holiday Homes information

Number of reviews
1,016
Accommodation
1429 Holiday Homes
Lowest Price
€173
Highest Price
€614