Connecticut holiday rentals

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Best Connecticut holiday rentals

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AED 132 - AED 4,058AED 4,058 - AED 7,984AED 7,984 - AED 11,909AED 11,909 - AED 15,835AED 15,835+ per night

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ApartmentCondoCottageHomestayHouse

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Most recommended holiday rentals in Connecticut

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Beautiful Studio Apartment in Historic House - New Haven
Beautiful Studio Apartment in Historic House
Newhallville
8.5Very Good(40)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 540+
Check availability
Studio Apt with kitchen,Living room, bathroom & bedroom, near Griffith hospital - Ansonia - Living room
Studio Apt with kitchen,Living room, bathroom & bedroom, near Griffith hospital
Ansonia, CT, United States
9.3Wonderful(6)
Apartment
Air conditioning
AED 632+
Check availability
A country guest house just 21-32 minutes Bridgeport or New Haven Universities. - Shelton - Living room
A country guest house just 21-32 minutes Bridgeport or New Haven Universities.
Shelton, CT, United States
9.2Wonderful(18)
House
Free Wi-Fi
Air conditioning
AED 830+
Check availability
Modern Westport Studio with Pool Table & Lounge - Westport - Living room
Modern Westport Studio with Pool Table & Lounge
Westport, CT, United States
9.1Wonderful(6)
Apartment
Parking
Free Wi-Fi
Air conditioning
AED 1,017+
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Cozy Country Cottage - Woodbridge - Kitchen
Cozy Country Cottage
Woodbridge, CT, United States
8.5Very Good(4)
Cottage
Free Wi-Fi
Air conditioning
AED 1,105+
Check availability
Coastal Work & Rest Retreat 1 - Bridgeport - Dining room
Coastal Work & Rest Retreat 1
Bridgeport, CT, United States
9.5Wonderful(1)
Apartment
Parking
Free Wi-Fi
Air conditioning
AED 1,186+
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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)
Apartment
Air conditioning
AED 1,190+
Check availability
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
House
Air conditioning
AED 1,227+
Check availability
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, Majestic Views - Salisbury - Living room
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, Majestic Views
Salisbury, CT, United States
9.6Wonderful(85)
Cottage
Free Wi-Fi
Air conditioning
AED 1,260+
Check availability
Cheerful 4 bedrooms residential house. - Bridgeport - Living room
Cheerful 4 bedrooms residential house.
Bridgeport, CT, United States
9.6Wonderful(32)
House
Air conditioning
AED 1,443+
Check availability
Serene Salisbury Rental Home on 26 Acres with Deck! - Salisbury
Serene Salisbury Rental Home on 26 Acres with Deck!
Salisbury, CT, United States
10Wonderful(3)
House
Free Wi-Fi
Air conditioning
AED 1,487+
Check availability
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)
Apartment
Free Wi-Fi
Air conditioning
AED 1,763+
Check availability
Renovated Apartment on Main St. - Salisbury - Living room
Renovated Apartment on Main St.
Salisbury, CT, United States
6.0Okay(2)
Apartment
Air conditioning
AED 1,858+
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Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood - Westport - Bedroom
Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood
Westport, CT, United States
10Wonderful(4)
House
Free Wi-Fi
Air conditioning
AED 3,404+
Check availability
Amazing Waterfront Home, Private Beach & Hot Tub Branford - Branford - Living room
Amazing Waterfront Home, Private Beach & Hot Tub Branford
Branford, CT, United States
9.6Wonderful(26)
House
Free Wi-Fi
Air conditioning
AED 5,116+
Check availability
Historic oyster shack. - Westport - Building
Historic oyster shack.
Westport, CT, United States
Cottage
AED 16,981+
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 AED 251. The highest prices are found on Wednesday, with average rates at AED 5,324.

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)

April
July
AED 1,208
AED 1,053
Cheapest month to stay with an average 58% drop in price.
Most expensive month to stay with an average 81% 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 Salisbury (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 AED 559. 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, agritourism, cottages, cabins, campgrounds, caravans, houseboats, hotels, 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 11% 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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