Connecticut holiday rentals

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Best Connecticut holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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R0 - R19 872R19 872 - R39 744R39 744 - R59 615R59 615 - R79 469R79 469+ per night

Property Types

ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Connecticut

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Historic Mansion 1841 - Higganum - Patio
Historic Mansion 1841
Higganum, CT, United States
Air conditioning
R3 520+
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The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC - Stamford
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC
Stamford, CT, United States
Air conditioning
R4 360+
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Summer at the Haddam House - Haddam - Beach
Summer at the Haddam House
Haddam, CT, United States
Free Wi-Fi
Air conditioning
R4 718+
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Your perfect Westport getaway is here! - Westport - Balcony
Your perfect Westport getaway is here!
Westport, CT, United States
R4 986+
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Shantok Queen suites walk to Mohegan casino/Wi-Fi - Montville
Shantok Queen suites walk to Mohegan casino/Wi-Fi
Montville, CT, United States
Air conditioning
R5 195+
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Darien Home - Darien - Kitchen
Darien Home
Darien, CT, United States
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R5 218+
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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
Air conditioning
R6 040+
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Walk To Goodspeed Opera House! - East Haddam - Kitchen
Walk To Goodspeed Opera House!
East Haddam, CT, United States
10Wonderful(1)
Air conditioning
R6 112+
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Room In Lake Home - 2br 1ba Kitchenette - Greenwich - Bedroom
Room In Lake Home - 2br 1ba Kitchenette
Greenwich, CT, United States
7.0Good(1)
Parking
Free Wi-Fi
Air conditioning
R7 152+
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Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt - East Haddam
Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt
East Haddam, CT, United States
9.5Wonderful(14)
Parking
Air conditioning
R7 237+
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Luke's Landing - Westport - Bedroom
Luke's Landing
Westport, CT, United States
Parking
Free Wi-Fi
Air conditioning
R8 238+
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Quarry House Mid-Century Modern - Haddam - Living room
Quarry House Mid-Century Modern
Haddam, CT, United States
Parking
Free Wi-Fi
Air conditioning
R13 760+
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Rowayton House Close To Town - Norwalk - Outdoor view
Rowayton House Close To Town
Norwalk, CT, United States
Free Wi-Fi
Pet-friendly
Air conditioning
R21 748+
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Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC - Darien
Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC
Darien, CT, United States
Free Wi-Fi
Air conditioning
R23 196+
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River Front Home Good for Family and Groups - East Haddam
River Front Home Good for Family and Groups
East Haddam, CT, United States
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R25 447+
Check availability
Historic oyster shack. - Westport - Building
Historic oyster shack.
Westport, CT, United States
R81 953+
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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 R28 566. The highest prices are found on Friday, with average rates at R247 755.

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

High season

Average price (weeknight)

Average price (weekend night)

December
September
R5 997
R5 352
Cheapest month to stay with an average 32% drop in price.
Most expensive month to stay with an average 31% 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 February and August.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Connecticut for 9 days.
  • Pool, fireplace, pet friendly, air-conditioned, and hot tub are the most popular holiday rental property amenities in Connecticut
  • Holiday rentals in Connecticut are around 26% 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 Fairfield (75% of total searches to Connecticut). The next most popular destination is New Haven (25%).

  • 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 R921. 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 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

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