Connecticut holiday rentals

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Booking Insights
Recommended by KAYAK

Best Connecticut holiday rentals

Most recommended holiday rentals in Connecticut

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1950s Charm In The Heart Of Waterbury - Waterbury
1950s Charm In The Heart Of Waterbury
Waterbury, CT, United States
3.7Poor(39)
Homestay
Parking
Free Wi-Fi
Private studio guesthouse in Watertown CT - Watertown
Parking
Free Wi-Fi
Town Plot Waterbury - Waterbury
Town Plot Waterbury
Waterbury, CT, United States
5.9Fair(56)
Homestay
Parking
Free Wi-Fi
Linmota Vacation Home - Watertown
Linmota Vacation Home
Watertown, CT, United States
5.0Fair(1)
Homestay
Parking
Free Wi-Fi
Pet friendly
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 $118. The highest prices are found on Wednesday, with average rates at $2,507.

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)

April
July
$556
$518
Cheapest month to stay with an average 57% drop in price.
Most expensive month to stay with an average 70% 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 January and July.
  • The cheapest night for renting a holiday home in Connecticut is Sunday. In contrast, the most expensive is Wednesday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Connecticut for 17 days.
  • Pool, pet friendly, air-conditioned, and hot tub are the most popular holiday rental property amenities in Connecticut
  • Holiday rentals in Connecticut are around 22% 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 Greenwich (33% of total searches to Connecticut). The next most popular destinations are Stratford (17%) and Waterbury (17%). Searches for holiday rentals in Oxford (17%) and Windsor (17%) are also popular.

  • 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 $354. 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