Holiday Homes in Connecticut

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Top Cities in Connecticut

Featured Holiday Homes in Connecticut

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

Greenwich
9.6 out of 10, Exceptional, (20)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is €183
includes taxes & fees
9 Nov - 10 Nov
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

Stonington
10.0 out of 10, Exceptional, (2)
"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...
United States
Jim S.
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Charming Historic House in Downtown Mystic

Mystic
10.0 out of 10, Exceptional, (160)
"Wonderful stay in a great cottage that is close and convenient to many sights. Owners very helpful, also"
United States
Beverly T.
The price is €320
includes taxes & fees
9 Nov - 10 Nov
Charming Historic House in Downtown Mystic

Unique Retreat w/ Private Patio, 4 King Beds & BBQ

Groton
10.0 out of 10, Exceptional, (126)
"The rooms were all equally size with King size beds so it’s perfect for 4 couples. House is warm, clean and comfortable. Would love to come back during warmer months to enjoy the deck and all the house has to offer. Thank you"
United States
Shirley T.
The price is €466
includes taxes & fees
16 Nov - 17 Nov
Unique Retreat w/ Private Patio, 4 King Beds & BBQ

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

East Lyme
10.0 out of 10, Exceptional, (106)
"We had such an amazing time here and are planning to return for our next family vacation! The house was clean and spacious and the communication was phenomenal. Everyone we interacted with at the farm was kind, caring, and helpful. There is so much to do at the farm and in the surrounding area. We could not recommend this place more! Best vacation ever!"
United States
Adrienne N.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Oak Grove Cottage - in the foothills of Mystic

Groton
10.0 out of 10, Exceptional, (15)
"This place was very comfortable and welcoming. I really dont have anything bad to say about this home. It is very well stocked, extra towels, to soaps, shampoos, conditioners in the bathroom. Extra beach towels, sunscreen if it was needed. Ive stayed at some wyndham condos that arent as well stocked on supplies. Will definitely be returning for a longer stay. "
United States
Jen L.
The price is €385
includes taxes & fees
10 Nov - 11 Nov
Oak Grove Cottage - in the foothills of Mystic

Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Mystic
9.8 out of 10, Exceptional, (158)
"Great Location! Within walking distance to all the sights in Mystic!"
United States
Jamye B.
The price is €241
includes taxes & fees
12 Nov - 13 Nov
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Cozy Ocean Front Retreat with Private Beach!

Milford
10.0 out of 10, Exceptional, (30)
"Beautiful location in a quiet spot directly on the beach. The house was immaculate, and well stocked. exactly as described. The view was amazing, we had a great stay. Great communication with the host. "
United States
greg
Cozy Ocean Front Retreat with Private Beach!

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Very nice stay and very clean"
United States
Markel W.
The price is €126
includes taxes & fees
9 Nov - 10 Nov
Business or Weekend escape

Your Charming 4BR Retreat Home Minutes from Casino Excitement!

Norwich
9.6 out of 10, Exceptional, (10)
"This was a great home for what we needed it for. Close to Foxwoods Casino which was our purpose for the stay. The home was comfortable and clean. No issues!"
United States
Tyra J.
The price is €864
includes taxes & fees
9 Nov - 10 Nov
Your Charming 4BR Retreat Home Minutes from Casino Excitement!

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
The price is €1,050
includes taxes & fees
27 Nov - 28 Nov
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

Middletown
6.6 out of 10, (4)
"Nice place"
United States
Jousette C.
The price is €205
includes taxes & fees
13 Nov - 14 Nov
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

The Sunshine House Near Mystic Seaport ⛵️

Groton
10.0 out of 10, Exceptional, (38)
"Great little welcoming home. Nicely appointed with the little amenities that m am me it feel like home. "
United States
Chris D.
The Sunshine House Near Mystic Seaport ⛵️

McAngel Haven: 5 mins from Yale

West Haven
9.6 out of 10, Exceptional, (16)
"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."
United States
Bradley D.
The price is €473
includes taxes & fees
10 Nov - 11 Nov
McAngel Haven: 5 mins from Yale

Casino Wine Down House

Montville
9.8 out of 10, Exceptional, (63)
"Enjoyed"
United States
Robert K.
Casino Wine Down House

The Goshen Glass Chalet

Goshen
9.6 out of 10, Exceptional, (41)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
United States
Tracy F.
The Goshen Glass Chalet

Perfect home for adventure! 2mi to Foxwoods, 15 min to Mystic, tour CT WineTrail

Preston
10.0 out of 10, Exceptional, (9)
"Easy communication with the owner very comfortable n everything is there"
United States
Nikom
Perfect home for adventure! 2mi to Foxwoods, 15 min to Mystic, tour CT WineTrail

Charming 1870 cape cottage in Litchfield

Litchfield
10.0 out of 10, Exceptional, (65)
"Beautiful house"
United States
Anonymous traveller
Charming 1870 cape cottage in Litchfield

The Tree House at Underhill Hollow

Thompson
9.4 out of 10, Exceptional, (33)
"We enjoyed Underhill Hollow, beautiful spot with whimsy & hospitality."
United States
amy m.
The price is €154
includes taxes & fees
15 Nov - 16 Nov
The Tree House at Underhill Hollow

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

New Fairfield
9.4 out of 10, Exceptional, (31)
"Only thing that was a challenge was carrying the kayaks down the hill and across the street. Living room was a bit hot due to no air conditioner. Host was extremely nice and accomodating and the place was well kept. "
United States
Jennifer W.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
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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Connecticut Holiday Homes information

Number of reviews
947
Accommodation
1333 Holiday Homes
Lowest Price
€126
Highest Price
€1,050