Connecticut holiday rentals

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Best Connecticut holiday rentals

Most recommended holiday rentals in Connecticut

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Modern Westport Studio with Pool Table & Lounge - Westport - Living room
Modern Westport Studio with Pool Table & Lounge
Westport, CT, United States
7.3Good(2)
Parking
Free Wi-Fi
Air conditioning
R3 977+
Check availability
Luke's Landing - Westport - Bedroom
Luke's Landing
Westport, CT, United States
Parking
Free Wi-Fi
Air conditioning
R8 120+
Check availability
Sweet Escape, 2br Apt In Beach Community, Only 1 Hr To Nyc! - Norwalk - Kitchen
Sweet Escape, 2br Apt In Beach Community, Only 1 Hr To Nyc!
Norwalk, CT, United States
9.5Wonderful(6)
Parking
Free Wi-Fi
Air conditioning
R8 752+
Check availability
Cozy, pleasant 2BR apt in Beach community! - Norwalk - Living room
Cozy, pleasant 2BR apt in Beach community!
Norwalk, CT, United States
10Wonderful(5)
Parking
Free Wi-Fi
Air conditioning
R6 652+
Check availability
Historic Connecticut Home with Grill and Spacious Yard - Weston - Patio
Historic Connecticut Home with Grill and Spacious Yard
Weston, CT, United States
Free Wi-Fi
Pet-friendly
Air conditioning
R9 049+
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Main Street Stay Westport - Westport - Living room
Main Street Stay Westport
Westport, CT, United States
Parking
Free Wi-Fi
Air conditioning
R12 097+
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Enjoy all Westport has to offer! - Westport - Dining room
Enjoy all Westport has to offer!
Westport, CT, United States
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R7 693+
Check availability
Westport In-Town Stay - Westport - Dining room
Westport In-Town Stay
Westport, CT, United States
Air conditioning
R12 487+
Check availability
Westport \'Gold Coast\' across from Southport beach - Southport - Living room
Westport \'Gold Coast\' across from Southport beach
Southport, CT, United States
Pet-friendly
Air conditioning
R6 076+
Check availability
Westport: Walk to Town (Really) Private Yard, One Floor - Westport - Bedroom
Westport: Walk to Town (Really) Private Yard, One Floor
Westport, CT, United States
10Wonderful(4)
Free Wi-Fi
Pet-friendly
Air conditioning
R15 925+
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
Air conditioning
R5 779+
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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
8.9Very Good(23)
Parking
Free Wi-Fi
Pool
Air conditioning
R6 281+
Check availability
Sunny Westport Studio Apt. Above Historic Mill - Westport
Sunny Westport Studio Apt. Above Historic Mill
Westport, CT, United States
9.3Wonderful(2)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R5 723+
Check availability
Cozy Villa 3 mins to Mohegan- Fully Stocked with King Bed & Fireplace- Jacuzzi, Saltwater Pools, Sauna - Norwich
Cozy Villa 3 mins to Mohegan- Fully Stocked with King Bed & Fireplace- Jacuzzi, Saltwater Pools, Sauna
Norwich, CT, United States
9.1Wonderful(13)
Parking
Free Wi-Fi
Pool
Air conditioning
R5 825+
Check availability
New Haven Stays - New Haven
New Haven Stays
Downtown
9.0Wonderful(115)
Free Wi-Fi
Air conditioning
R3 858+
Check availability
Getaway Villa- 3 mins to Mohegan- Fully Stocked with Two Full Beds & Fireplace- Jacuzzi, Saltwater Pools, Sauna - Norwich
Getaway Villa- 3 mins to Mohegan- Fully Stocked with Two Full Beds & Fireplace- Jacuzzi, Saltwater Pools, Sauna
Norwich, CT, United States
9.5Wonderful(28)
Parking
Free Wi-Fi
Pool
Air conditioning
R6 002+
Check availability
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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 R21 180. In comparison, June is the most expensive month, with prices at R84 856.

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 R19 100. The highest prices are found on Friday, with average rates at R50 805.

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

October

High season

August

Average price (weeknight)

R4 958

Average price (weekend night)

R6 141
Cheapest month to stay with an average 9% drop in price.
Most expensive month to stay with an average 106% 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

  • What is the most popular holiday rental destination in Connecticut?

    Based on KAYAK holiday rental searches, the most popular destination is New Haven (100% of total searches to 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 R2 674. 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.

See more FAQs

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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