Connecticut holiday rentals

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Best Connecticut holiday rentals

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€0 - €939€939 - €1,878€1,878 - €2,817€2,817 - €3,756€3,756+ per night

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ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Connecticut

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Cozy studio quiet - Trumbull
Cozy studio quiet
Trumbull, CT, United States
10Wonderful(1)
Parking
Air conditioning
€167+
Check availability
The Safe House - High Tech Apt #3 - 4 beds - Greenwich - Bedroom
The Safe House - High Tech Apt #3 - 4 beds
Greenwich, CT, United States
Free Wi-Fi
Air conditioning
€223+
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Adorable 1-Bedroom Cottage in Weston, CT - Weston - Dining room
Adorable 1-Bedroom Cottage in Weston, CT
Weston, CT, United States
Free Wi-Fi
Pet friendly
Air conditioning
€259+
Check availability
Coastal Work & Rest Retreat 1 - Bridgeport
Coastal Work & Rest Retreat 1
Bridgeport, CT, United States
9.5Wonderful(1)
Parking
Free Wi-Fi
Air conditioning
€261+
Check availability
The Blue Sapphire 2BR 2 King beds & ample backyard - Bridgeport - Bedroom
The Blue Sapphire 2BR 2 King beds & ample backyard
Bridgeport, CT, United States
8.9Very Good(4)
Parking
Free Wi-Fi
Air conditioning
€301+
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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
8.7Very Good(26)
Parking
Free Wi-Fi
Pool
Air conditioning
€307+
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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
Air conditioning
€323+
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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
Air conditioning
€326+
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Lake Home - Greenwich - Bedroom
Lake Home
Greenwich, CT, United States
7.0Good(1)
Parking
Free Wi-Fi
Air conditioning
€340+
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Walk To Mohegan!05mi-modern 3br Home Getaway - Norwich
Walk To Mohegan!05mi-modern 3br Home Getaway
Norwich, CT, United States
10Wonderful(1)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€343+
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Storybook Cottage - Old Saybrook - Bedroom
Storybook Cottage
Old Saybrook, CT, United States
Free Wi-Fi
Air conditioning
€354+
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Stay at Black Rock Harbor - Bridgeport - Building
Stay at Black Rock Harbor
Bridgeport, CT, United States
9.7Wonderful(6)
Parking
Free Wi-Fi
Air conditioning
€584+
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Lakeside Cottage On The Water With Beautiful Views Up The Lake! - Ledyard - Outdoor view
Lakeside Cottage On The Water With Beautiful Views Up The Lake!
Ledyard, CT, United States
Pet friendly
Air conditioning
€591+
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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
Air conditioning
€592+
Check availability
Lakeside Cottage Overhanging The Water, Beautiful Window Views Across The Lake - Ledyard - Outdoor view
Lakeside Cottage Overhanging The Water, Beautiful Window Views Across The Lake
Ledyard, CT, United States
9.8Wonderful(43)
Pet friendly
Air conditioning
€596+
Check availability
Upscale 4BR Retreat at the Reservoir! - Bridgeport
Upscale 4BR Retreat at the Reservoir!
Bridgeport, CT, United States
9.7Wonderful(2)
Parking
Free Wi-Fi
Air conditioning
€658+
Check availability
Useful Info

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 November, with average rates of €40. In comparison, April is the most expensive month, with prices at €496.

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 €67. The highest prices are found on Saturday, with average rates at €254.

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

November

High season

July

Average price (weeknight)

€257

Average price (weekend night)

€289
Cheapest month to stay with an average 42% drop in price.
Most expensive month to stay with an average 35% 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 €44. Search here for similar prices

  • How much is a holiday rental in Connecticut for this weekend?

    In the last 72 hours, users have found Connecticut holiday rentals for this weekend for as little as €69 per night. 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, campgrounds, 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 19% 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

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