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Connecticut holiday rentals

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Booking Insights
Recommended by KAYAK

Best Connecticut holiday rentals

These are the best prices for 6-13 Oct.
Stamford Suites - Stamford - Lobby
Stamford Suites
Downtown
5.3Fair(462)
Apartment
$343+
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Econo Lodge - West Haven - Bedroom
Econo Lodge
West Haven, CT, United States
3.2Poor(637)
Lodge
$176+
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5BR Waterview Home near Cove Beach, Sauna, Game Room, Fenced Backyard - Stamford
5BR Waterview Home near Cove Beach, Sauna, Game Room, Fenced Backyard
Stamford, CT, United States
9.1Wonderful(28)
House
$1,484+
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Mystic Refuge with Patio Less Than 1 Mi to Downtown! - Mystic - Living room
Mystic Refuge with Patio Less Than 1 Mi to Downtown!
Downtown
9.3Wonderful(33)
Apartment
$671+
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Mystic Refuge w/ Patio 1 Mi to Downtown! - Mystic - Living room
Mystic Refuge w/ Patio 1 Mi to Downtown!
Downtown
9.5Wonderful(18)
Condo
$641+
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Econo Lodge Bethel - Danbury - Hawleyville - Bedroom
Econo Lodge Bethel - Danbury
Hawleyville, CT, United States
7.8Good(110)
Lodge
$249+
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Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration! - Mystic - Building
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
Mystic, CT, United States
10Wonderful(68)
House
$1,296+
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Welcome to Hat City Danbury | A Suburban Retreat Close to It All - Danbury - Building
Welcome to Hat City Danbury | A Suburban Retreat Close to It All
Danbury, CT, United States
9.3Wonderful(29)
Apartment
$521+
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Gem by the water with firepit & all fenced backyard 2 Bedrooms - Stamford - Living room
Gem by the water with firepit & all fenced backyard 2 Bedrooms
Stamford, CT, United States
9.3Wonderful(24)
Villa
$572+
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Super Cute & Cozy Apartment In Downtown Mystic! - Mystic - Living room
Super Cute & Cozy Apartment In Downtown Mystic!
Downtown
9.5Wonderful(72)
Apartment
$508+
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Historic Three Bedroom Townhouse -- Downtown Mystic - Mystic - Living room
Historic Three Bedroom Townhouse -- Downtown Mystic
Downtown
9.9Wonderful(58)
House
$756+
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New England Hospitality at the Carriage House Mystic Vacation Rentals LLC - Old Mystic - Bedroom
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic, CT, United States
9.9Wonderful(35)
Apartment
$408+
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Lovely & Light-Filled Victorian Townhouse With Luxury Amenities - Mystic - Living room
Lovely & Light-Filled Victorian Townhouse With Luxury Amenities
Downtown
9.9Wonderful(60)
House
$1,078+
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Walkable New Haven Retreat w/ Ocean Views! - New Haven
Walkable New Haven Retreat w/ Ocean Views!
East Shore
9.9Wonderful(11)
House
$1,068+
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Belltown Retreat - Stamford
Belltown Retreat
Stamford, CT, United States
9.6Wonderful(46)
House
$895+
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Exceptional Contemporary Retreat with 4 King Beds in Mystic CT - Groton
Exceptional Contemporary Retreat with 4 King Beds in Mystic CT
Groton, CT, United States
10Wonderful(54)
House
$1,147+
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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?

Wednesday offers the lowest rates in Connecticut, with an average nightly price of $156. The highest prices are found on Monday, with average rates at $505.

How early should you book a vacation rental in Connecticut?

Book at least 70 days before your stay begins to get the best price for your Connecticut vacation rental.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
November
$412
$484
Cheapest month to stay with an average 21% drop in price.
Most expensive month to stay with an average 60% 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 East Windsor (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 $184. 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 $123 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, houses, homestays, agritourism, caravans, cottages, cabins, campgrounds, villas, lodges, hotels, houseboats 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 25% 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.

More options for your stay in Connecticut

Complete your trip to Connecticut

Car rentals in Connecticut