What is the most popular holiday rental destination in Connecticut?

Based on KAYAK holiday rental searches, the most popular destination is Stratford (25% of total searches to Connecticut). The next most popular destinations are Waterbury (25%) and Oxford (25%). Searches for holiday rentals in Windsor (25%) 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 $122.

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 $116 per night.

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, 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 10% allowing you to bring your pet along with you.

Connecticut Holiday Rentals

Recommended by KAYAK

Best Connecticut holiday rentals

Orange Oasis in the Heart of East Rock with FREE parking near DT and Yale

East Rock

9.5Wonderful(24)

Apartment

Parking

Free Wi-Fi

Low season	High season	Average price (weeknight)	Average price (weekend night)
April	July	$445	$461
Cheapest month to stay with an average 44% drop in price.	Most expensive month to stay with an average 105% rise in price.	Average Sun - Thu price over the last 2 weeks.	Average Fri & Sat price over the last 2 weeks.

Connecticut holiday rentals

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

Best Connecticut holiday rentals

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 $107. In comparison, July is the most expensive month, with prices at $383.

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 $114. The highest prices are found on Wednesday, with average rates at $1,945.

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)

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 Stratford (25% of total searches to Connecticut). The next most popular destinations are Waterbury (25%) and Oxford (25%). Searches for holiday rentals in Windsor (25%) 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 $122. 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 $116 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, 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 10% allowing you to bring your pet along with you.

Where to stay in Connecticut?

Everything you need to know for your stay in Connecticut

Complete your trip to Connecticut

Other popular Holiday Rental destinations