Connecticut holiday rentals

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Best Connecticut holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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R656 - R19 631R19 631 - R38 589R38 589 - R57 547R57 547 - R76 505R76 505+ per night

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Most recommended holiday rentals in Connecticut

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The Carriage House at Chaprae Hall - Killingly - Bedroom
The Carriage House at Chaprae Hall
Killingly, CT, United States
9.7Wonderful(9)
Free Wi-Fi
Air conditioning
R3 209+
Check availability
Killingly Barnyard Studio in Wine Country! - Ballouville - Living room
Killingly Barnyard Studio in Wine Country!
Ballouville, CT, United States
9.8Wonderful(10)
Free Wi-Fi
Pet-friendly
Air conditioning
R3 467+
Check availability
Modern Westport Studio with Pool Table & Lounge - Westport - Living room
Modern Westport Studio with Pool Table & Lounge
Westport, CT, United States
8.6Very Good(4)
Parking
Free Wi-Fi
Air conditioning
R3 692+
Check availability
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC - Stamford - Living room
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC
Stamford, CT, United States
Air conditioning
R3 726+
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Live the Walkable Darien Lifestyle in this Charming Noroton Heights Gem! - Darien
Live the Walkable Darien Lifestyle in this Charming Noroton Heights Gem!
Darien, CT, United States
3.0Poor(1)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 899+
Check availability
Your perfect Westport getaway is here! - Westport - Balcony
Your perfect Westport getaway is here!
Westport, CT, United States
10Wonderful(13)
R4 433+
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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
9.0Wonderful(4)
Parking
Free Wi-Fi
Air conditioning
R4 830+
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Remodeled spacious 2 BR near downtown with yard and wrap around porch - Branford - Living room
Remodeled spacious 2 BR near downtown with yard and wrap around porch
Branford, CT, United States
10Wonderful(2)
Air conditioning
R5 589+
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The B&W Haven 3BR private office by LI Ferry - Bridgeport - Living room
The B&W Haven 3BR private office by LI Ferry
Bridgeport, CT, United States
8.7Very Good(2)
Parking
Free Wi-Fi
Air conditioning
R5 693+
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Welcome to our junior one-bedroom located in the beautiful town of Darien. - Darien - Dining room
Welcome to our junior one-bedroom located in the beautiful town of Darien.
Darien, CT, United States
Air conditioning
R6 386+
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Luxury Designer 2 bedroom+office/3bed vacation home. - Bridgeport - Dining room
Luxury Designer 2 bedroom+office/3bed vacation home.
Bridgeport, CT, United States
9.1Wonderful(17)
Free Wi-Fi
Air conditioning
R7 042+
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Secluded 2-Acre Lakefront Home! Book Your Getaway! - Woodstock - Building
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock, CT, United States
9.7Wonderful(64)
Free Wi-Fi
Air conditioning
R9 557+
Check availability
The B&W Haven 5BR Home with yard theater - Bridgeport - Living room
The B&W Haven 5BR Home with yard theater
Bridgeport, CT, United States
9.1Wonderful(9)
Parking
Free Wi-Fi
Air conditioning
R10 091+
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Rowayton House Close To Town - Norwalk - Living room
Rowayton House Close To Town
Norwalk, CT, United States
10Wonderful(17)
Free Wi-Fi
Air conditioning
R19 855+
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modern home with a private Heated pool and jacuzzi - Hamden
modern home with a private Heated pool and jacuzzi
Hamden, CT, United States
Parking
Free Wi-Fi
Air conditioning
R24 344+
Check availability
Avail 4th Of July Week! 5-Bedroom Estate With Saltwater Pool, Spa, Game Room - Westport - Building
Avail 4th Of July Week! 5-Bedroom Estate With Saltwater Pool, Spa, Game Room
Westport, CT, United States
10Wonderful(1)
Air conditioning
R46 075+
Check availability
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?

Sunday offers the lowest rates in Connecticut, with an average nightly price of R1 327. The highest prices are found on Wednesday, with average rates at R8 231.

How early should you book a vacation rental in Connecticut?

Book at least 64 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
R5 400
R5 155
Cheapest month to stay with an average 28% drop in price.
Most expensive month to stay with an average 67% 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 Fairfield (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 R3 585. 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 R889 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, lodges, villas, cabins, cottages, agritourism, 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 10% 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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