Connecticut holiday rentals

Search hundreds of travel sites at once for holiday home deals in Connecticut

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Connecticut holiday rentals

Walk to the Outfield of Lime Rock Park - Salisbury - Living room
Walk to the Outfield of Lime Rock Park
Salisbury, CT, United States
Parking
Free Wi-Fi
Air conditioning
Quarry House Mid-Century Modern - Haddam - Living room
Parking
Free Wi-Fi
Air conditioning
Modern Westport Studio with Pool Table & Lounge - Westport - Living room
Parking
Free Wi-Fi
Air conditioning
The Farmhouse Stay - Haddam - Living room
The Farmhouse Stay
Haddam, CT, United States
Agritourism
Air conditioning
Renovated Apartment on Main St. - Salisbury - Living room
Renovated Apartment on Main St.
Salisbury, CT, United States
7.3Good(3)
Apartment
Air conditioning
Sunny Westport Studio Apt. Above Historic Mill - Westport - Dining room
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
The Blue Sapphire 2BR 2 King beds & ample backyard - Bridgeport - Bedroom
Parking
Free Wi-Fi
Air conditioning
Luke's Landing - Westport - Bedroom
Luke's Landing
Westport, CT, United States
Air conditioning
Beechmont-Charming Colonial for Events and Getaways! - Bridgeport - Building
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Quintessential New England Home with Patio and Grill! - Putnam
Free Wi-Fi
Pet-friendly
Air conditioning
Coastal Work & Rest Retreat 1 - Bridgeport
Coastal Work & Rest Retreat 1
Bridgeport, CT, United States
Parking
Free Wi-Fi
Air conditioning
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.

Which month has the cheapest vacation rental rates in Connecticut?

Vacation rentals are cheapest in Connecticut in February, with average rates of AED 242. In comparison, June is the most expensive month, with prices at AED 984.

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 255. The highest prices are found on Wednesday, with average rates at AED 5,295.

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.

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

March
July
AED 1,015
AED 1,062
Cheapest month to stay with an average 66% drop in price.
Most expensive month to stay with an average 102% 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 363. 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 AED 256 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, 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 9% 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