Holiday Homes in Connecticut

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Top Cities in Connecticut

Featured Holiday Homes in Connecticut

The Tree House at Underhill Hollow

9.2 out of 10, Wonderful, (25)
"Loved the treasure hunt and fairy gardens. "
The price is €152
includes taxes & fees
11 Aug - 12 Aug
The Tree House at Underhill Hollow

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (6)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is €553
includes taxes & fees
17 Aug - 18 Aug
Thames River Retreat · CT College+Casinos+USCGA

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT

Regency Inn and Suites - Non Smoking King

8.0 out of 10, Very good, (3)
"Desk clerk was wonderful. Made sure my stay was everything that I needed."
The price is €107
includes taxes & fees
14 Aug - 15 Aug
Regency Inn and Suites - Non Smoking King

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

9.8 out of 10, Exceptional, (159)
"Great location. Very nice property. Made the weekend stay a success "
The price is €227
includes taxes & fees
24 Aug - 25 Aug
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
Stareway to Heaven Su

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

7.6 out of 10, Good, (7)
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

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

9.0 out of 10, Wonderful, (18)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Cozy 3 bedroom minutes from Yale and the beach

7.4 out of 10, Good, (3)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach

Downtown Mystic Home Private Driveway Fenced in Yard Discounted longer stays

10.0 out of 10, Exceptional, (102)
"A sweet cheerful place near the heart of mystic. We stayed for a week and found kitchen to be well equipped, house clean, comfortable, and conveniently located. "
Downtown Mystic Home Private Driveway Fenced in Yard Discounted longer stays

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (43)
"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

The Seaport Bridgeman - All things Mystic steps from your door

10.0 out of 10, Exceptional, (24)
"We had a great stay. Highly recommended!"
The Seaport Bridgeman - All things Mystic steps from your door

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

10.0 out of 10, Exceptional, (38)
"Very clean well kept property near beach - host very welcoming and receptive. Enjoyed our stay!"
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield

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 €740
includes taxes & fees
9 Sept - 10 Sept
Spacious Home Near Mohegan Sun

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Very comfortable rockers and Adirondack chairs make it easy to relax and enjoy the lake view. Our bed was comfortable, and Nile supplied all we needed with linens and soaps. We appreciated all the space and large dining table. Lake is beautiful. Very enjoyable stay. Exceptional communication with our host. "
Grammy's Lake House w/ Private Waterfront Access

Lake Oasis with Firepit, Game room and Kayaks

10.0 out of 10, Exceptional, (1)
"This was our family's first time to Candlewood Lake/Squantz Pond. The area is picturesque and the location of this property is perfect. The porch off of the living area directly overlooks Squantz Pond and mountains. The basement was ideal for teenagers with a projector screen, air hockey/pool, and exercise equipment. The bedroom were spacious and beds comfortable. The kitchen/living area are open concept and the whole family could be together. The owner and his daughter are incredibly kind and...
Lake Oasis with Firepit, Game room and Kayaks

Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing

5.4 out of 10, (3)
"The listing states a 1 bedroom, don’t be confused thinking there is a room with a door and then another room, as it’s just a single room with a bed. There was one gentleman that was very blunt and rude with his words. I unfortunately dealt with him prior to my visit, via phone, and once I got there. However, I had interaction with two others and the experience with them was very pleasant! Breakfast staff was extremely welcoming and friendly! (They check your paper for breakfast- be sure to bring...
The price is €107
includes taxes & fees
12 Aug - 13 Aug
Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing

Business or Weekend escape

9.2 out of 10, Wonderful, (44)
"Very nice owner with great communication. "
The price is €129
includes taxes & fees
18 Aug - 19 Aug
Business or Weekend 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Connecticut Hotel Reviews