Connecticut holiday rentals

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Best Connecticut holiday rentals

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$64 - $1,880$1,880 - $3,695$3,695 - $5,511$5,511 - $7,327$7,327+ per night

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Most recommended holiday rentals in Connecticut

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Your perfect Westport getaway is here! - Westport - Balcony
Your perfect Westport getaway is here!
Westport, CT, United States
10Wonderful(11)
$461+
Check availability
Sunny Westport Studio Apt. Above Historic Mill - Westport
Sunny Westport Studio Apt. Above Historic Mill
Westport, CT, United States
9.5Wonderful(3)
Parking
Free Wi-Fi
Pet friendly
$463+
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California guest house - Greenwich
California guest house
Greenwich, CT, United States
7.8Good(4)
Parking
Free Wi-Fi
Pet friendly
$468+
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Private Apt In Southfordsouthbury - Southbury - Living room
Private Apt In Southfordsouthbury
Southbury, CT, United States
9.1Wonderful(17)
Parking
Free Wi-Fi
Pet friendly
$510+
Check availability
Peaceful & Private house in charming Simsbury. No pets - Simsbury
Peaceful & Private house in charming Simsbury. No pets
Simsbury, CT, United States
10Wonderful(1)
$532+
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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
8.9Very Good(4)
Parking
Free Wi-Fi
$543+
Check availability
Vibrant & Cozy 3-bedroom house 7-min from beach - Milford
Vibrant & Cozy 3-bedroom house 7-min from beach
Milford, CT, United States
9.7Wonderful(7)
$646+
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Boho Chic Private Home in the Heart of Westport CT - Westport - Living room
Boho Chic Private Home in the Heart of Westport CT
Westport, CT, United States
$684+
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Mountaintop Horse Farm with Heated Pool - Bloomfield - Building
Mountaintop Horse Farm with Heated Pool
Bloomfield, CT, United States
10Wonderful(24)
Free Wi-Fi
$686+
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Get Ready for Blissful Getaway! 2 Cozy Units, Free Breakfast and Parking! - Avon
Get Ready for Blissful Getaway! 2 Cozy Units, Free Breakfast and Parking!
Avon, CT, United States
Free Wi-Fi
$790+
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My little place Cozy Open concept for quiet time. - Stratford - Living room
My little place Cozy Open concept for quiet time.
Stratford, CT, United States
9.6Wonderful(9)
$822+
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Luke's Landing - Westport - Bedroom
Luke's Landing
Westport, CT, United States
9.7Wonderful(8)
$867+
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Lakeside Retreat - Columbia - Kitchen
Lakeside Retreat
Columbia, CT, United States
9.2Wonderful(6)
Parking
Free Wi-Fi
Pet friendly
$926+
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Upscale 4BR Retreat at the Reservoir! - Bridgeport - Bedroom
Upscale 4BR Retreat at the Reservoir!
Bridgeport, CT, United States
9.7Wonderful(3)
Parking
Free Wi-Fi
$1,554+
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Luxury 4-bedroom House with Indoor Pool & Picturesque Backyard w/Grill & Firepit - Oxford - Bedroom
Luxury 4-bedroom House with Indoor Pool & Picturesque Backyard w/Grill & Firepit
Oxford, CT, United States
$2,909+
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Historic oyster shack. - Westport - Building
Historic oyster shack.
Westport, CT, United States
$7,721+
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Booking Insights

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.

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 $145. The highest prices are found on Friday, with average rates at $2,265.

How early should you book a vacation rental in Connecticut?

Book at least 89 days before your stay begins to get the best price for your Connecticut vacation rental.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

March
July
$561
$492
Cheapest month to stay with an average 23% drop in price.
Most expensive month to stay with an average 66% 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

  • If you’re looking for a cheap holiday rental in Connecticut, you should consider visiting during the low season. The cheapest holiday homes in Connecticut can be found in July and August.
  • The cheapest night for renting a holiday home in Connecticut is Sunday. In contrast, the most expensive is Wednesday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Connecticut for 8 days.
  • Pool, pet friendly, air-conditioned, and hot tub are the most popular holiday rental property amenities in Connecticut
  • Holiday rentals in Connecticut are around 27% more expensive than hotels on average. Search here to compare prices for all accommodation types in Connecticut.

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 Greenwich (40% of total searches to Connecticut). The next most popular destinations are Stratford (20%) and Waterbury (20%). Searches for holiday rentals in Oxford (20%) are also popular.

  • 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 $149. 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 $86 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, cabins, bungalows, campgrounds, caravans, houseboats, castles and chalets.

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

    There are a number of dog and pet-friendly Connecticut holiday rentals, with around 16% 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

Car rentals in Connecticut

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