Connecticut holiday rentals

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Best Connecticut holiday rentals

Most recommended holiday rentals in Connecticut

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The Blue Sapphire 2BR 2 King beds & ample backyard - Bridgeport - Bedroom
The Blue Sapphire 2BR 2 King beds & ample backyard
Bridgeport, CT, United States
8.6Very Good(3)
Parking
Free Wi-Fi
RM 1,194+
Check availability
Luxury Villa- 3 mins to Mohegan- Fully Stocked with Fireplace- Jacuzzi, Saltwater Pools, Sauna - Norwich - Living room
Luxury Villa- 3 mins to Mohegan- Fully Stocked with Fireplace- Jacuzzi, Saltwater Pools, Sauna
Norwich, CT, United States
8.9Very Good(23)
Parking
Free Wi-Fi
Pool
RM 1,420+
Check availability
Econo Lodge - West Haven - Bedroom
Econo Lodge
West Haven, CT, United States
3.7Poor(492)
Parking
Free Wi-Fi
RM 383+
Check availability
Historic oyster shack. - Westport - Building
Historic oyster shack.
Westport, CT, United States
RM 20,035+
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Charming Colonial for Events and Getaways! - Bridgeport - Building
Charming Colonial for Events and Getaways!
Bridgeport, CT, United States
Parking
Free Wi-Fi
Pet-friendly
RM 2,998+
Check availability
Westport, Ct - Walk To The Beach - Nyc Getaway - Westport - Living room
Westport, Ct - Walk To The Beach - Nyc Getaway
Westport, CT, United States
Pet-friendly
RM 5,797+
Check availability
Peaceful Spa Escape Minutes To Mohegan Sun Casino - Norwich - Patio
Peaceful Spa Escape Minutes To Mohegan Sun Casino
Norwich, CT, United States
Free Wi-Fi
Pool
Spa
RM 1,328+
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The B&W Haven 3BR private office by LI Ferry - Bridgeport - Bedroom
The B&W Haven 3BR private office by LI Ferry
Bridgeport, CT, United States
8.7Very Good(2)
Parking
Free Wi-Fi
RM 1,428+
Check availability
Sunny & Spacious 2bd 1ba Wfh Apt-Huge Yard & Patio - Fairfield - Balcony
Sunny & Spacious 2bd 1ba Wfh Apt-Huge Yard & Patio
Fairfield, CT, United States
10Wonderful(1)
Parking
Free Wi-Fi
RM 1,242+
Check availability
Greenwich Ct. Rye N.Y. 2 Bedroom Loft Apartment!! - Port Chester - Pool
Greenwich Ct. Rye N.Y. 2 Bedroom Loft Apartment!!
Port Chester, NY, United States
8.7Very Good(11)
RM 1,553+
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The B&W Haven 5BR Home with yard theater - Bridgeport - Bedroom
The B&W Haven 5BR Home with yard theater
Bridgeport, CT, United States
Parking
Free Wi-Fi
RM 2,090+
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Lake Home - Greenwich - Outdoor view
Lake Home
Greenwich, CT, United States
Parking
Free Wi-Fi
RM 780+
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Luke's Landing - Westport - Bedroom
Luke's Landing
Westport, CT, United States
Parking
Free Wi-Fi
RM 1,891+
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Connecticut Lake House - Bridgeport
Connecticut Lake House
Bridgeport, CT, United States
5.1Fair(10)
Parking
Free Wi-Fi
RM 710+
Check availability
Coastal Work & Rest Retreat 1 - Bridgeport
Coastal Work & Rest Retreat 1
Bridgeport, CT, United States
10Wonderful(1)
Parking
Free Wi-Fi
RM 1,358+
Check availability
California guest house - Greenwich
California guest house
Greenwich, CT, United States
10Wonderful(1)
Parking
Free Wi-Fi
Pet-friendly
RM 1,138+
Check availability
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RM 0 - RM 4,729RM 4,729 - RM 9,457RM 9,457 - RM 14,186RM 14,186 - RM 18,911RM 18,911+ per night

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KAYAK’s insights for holiday rentals in Connecticut

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Connecticut with confidence.

Which month has the cheapest vacation rental rates in Connecticut?

Vacation rentals are cheapest in Connecticut in August, with average rates of RM 1,148. In comparison, June is the most expensive month, with prices at RM 4,600.

What is the cheapest day of the week to book a vacation rental in Connecticut?

Monday offers the lowest rates in Connecticut, with an average nightly price of RM 1,035. The highest prices are found on Friday, with average rates at RM 2,754.

How early should you book a vacation rental in Connecticut?

Book at least 75 days before your stay begins to get the best price for your Connecticut vacation rental.
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Good to know

Low season

April

High season

August

Average price (weeknight)

RM 1,148

Average price (weekend night)

RM 1,431
Cheapest month to stay with an average 10% drop in price.
Most expensive month to stay with an average 107% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Connecticut holiday rental

FAQs when booking a holiday home in Connecticut

  • How much is a holiday rental in Connecticut for tonight?

    In the last 72 hours, users have found Connecticut holiday rentals for tonight for as little as RM 223. Search here for similar prices

  • What types of holiday rentals are available in Connecticut?

    There are loads of different property types that you can make your holiday home in Connecticut. You’ll find apartments, condos, cottages, houses, homestays, lodges, villas, agritourism, bungalows, caravans, cabins, chalets, houseboats, luxury tents, treehouses and castles.

  • Are there any pet-friendly holiday rentals in Connecticut?

    There are a number of dog and pet-friendly Connecticut holiday rentals, with around 18% allowing you to bring your pet along with you.

Where to stay in Connecticut?

Our map will help you find the perfect place to stay in Connecticut by showing you the exact location of each holiday home.

Everything you need to know for your stay in Connecticut

Complete your trip to Connecticut

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