A city skyline at dusk with reflections in a calm body of water, a bridge, and modern buildings.

Holiday Rentals in Connecticut

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Top Cities in Connecticut

A cityscape with a mix of historic and modern buildings, including a prominent clock tower and a large, rectangular skyscraper.
Holiday RentalsHoliday Rentals

New Haven

New Haven
A marina with several boats docked, surrounded by houses and dense forest.
Holiday RentalsHoliday Rentals

Mystic

Mystic

Our top choices for Connecticut holiday rentals

A cabin with a dining table set for two, a bicycle, and a small porch area.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (197 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is €179
includes taxes & fees
3 Nov - 4 Nov
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is €236
includes taxes & fees
7 Oct - 8 Oct
DUNE Fairfield Beach
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is €367
includes taxes & fees
6 Oct - 7 Oct
Guesthouse at Norwalk Inn
A multi-story building with a brick facade, large windows, and a storefront with signage.

4. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
2.0 out of 10, (1 review)
"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
United States
Nicolas
The price is €244
includes taxes & fees
6 Oct - 7 Oct
Trumbull Apartments
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

5. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is €128
includes taxes & fees
6 Oct - 7 Oct
The Tiny Cottage & Mini Farm
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

6. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is €201
includes taxes & fees
6 Oct - 7 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A white house with a wooden staircase leading to a porch.

7. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is €109
includes taxes & fees
14 Oct - 15 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern living room with a sofa, a coffee table, and a rug.

8. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (11 reviews)
"Good location"
United States
Arthur
The price is €110
includes taxes & fees
11 Oct - 12 Oct
Entire guest suite in South Windsor, Connecticut
A modern living room with a large window, a sofa, a coffee table, and a TV.

9. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (14 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is €176
includes taxes & fees
6 Oct - 7 Oct
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A two-story house with a front porch, a balcony, and a driveway.

10. Grey comfort room

Grey comfort room
New London
9.6 out of 10, Exceptional, (4 reviews)
"Nice place"
United States
JACQUELINE FELICIANO
The price is €103
includes taxes & fees
6 Oct - 7 Oct
Grey comfort room
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

11. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is €188
includes taxes & fees
6 Oct - 7 Oct
Spacious 2 Bedroom apartment close to Yale Bowl
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

12. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is €176
includes taxes & fees
7 Oct - 8 Oct
The Tree House at Underhill Hollow
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

13. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (38 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is €231
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

14. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is €171
includes taxes & fees
6 Oct - 7 Oct
Wizard's Roost at Underhill Hollow
A patio with outdoor furniture, a covered seating area, and a brick pathway leading to a house with large windows and a chimney.

15. Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Norwich
9.6 out of 10, Exceptional, (63 reviews)
"Beautfil and convenient place. We stayed just one night and the location is perfect since it's just by the Spa."
United States
Aura
The price is €235
includes taxes & fees
6 Oct - 7 Oct
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
A two-story house with a porch, a front door with a wreath, and a small garden area.

16. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is €305
includes taxes & fees
6 Oct - 7 Oct
Bear Retreat - 2-bedroom house in Waterbury
A living room with a fireplace, two armchairs, a sofa, and a TV.

17. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is €194
includes taxes & fees
6 Oct - 7 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

18. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is €269
includes taxes & fees
6 Oct - 7 Oct
Once the old Schools house now a newly furnished Apartment
A lakeside view with a sandy beach, kayaks, and a 'No Dogs' sign.

19. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.0 out of 10, Wonderful, (49 reviews)
"Very peaceful and beautiful area. Well needed relaxing time. Highly recommend! Also Host was exceptional and attentive."
United States
Melissa
The price is €275
includes taxes & fees
19 Oct - 20 Oct
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
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

Two Trees Inn

Two Trees Inn

10/10 Excellent
"Great location, great value. Family friendly."
Gregory 1-night trip
Posted 3 hours ago
Two Trees Inn

Find out more about Connecticut

Holiday Homes in Connecticut

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