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

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

AED 132 - AED 4,175AED 4,175 - AED 8,214AED 8,214 - AED 12,257AED 12,257 - AED 16,297AED 16,297+ per night

Property type

ApartmentCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Connecticut

Show all
Modern Apartment in Black Rock- - Bridgeport - Living room
Modern Apartment in Black Rock-
Bridgeport, CT, United States
9.3Wonderful(3)
Free Wi-Fi
Pet-friendly
Air conditioning
AED 617+
Check availability
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
AED 1,006+
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)
Free Wi-Fi
Air conditioning
AED 1,050+
Check availability
The Riverside - Westport
The Riverside
Westport, CT, United States
8.0Very Good(1)
Air conditioning
AED 1,105+
Check availability
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
AED 1,249+
Check availability
Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed - New Haven - Living room
Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed
East Rock
9.5Wonderful(28)
Parking
Free Wi-Fi
Air conditioning
AED 1,270+
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
Air conditioning
AED 1,502+
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)
Free Wi-Fi
Air conditioning
AED 1,656+
Check availability
Serene Salisbury Rental Home on 26 Acres w/ Deck! - Salisbury - Living room
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Salisbury, CT, United States
9.7Wonderful(8)
Free Wi-Fi
Air conditioning
AED 1,766+
Check availability
Maison de Jardin Yale New Haven for Large Groups - Hamden - Living room
Maison de Jardin Yale New Haven for Large Groups
Hamden, CT, United States
9.4Wonderful(20)
Parking
Free Wi-Fi
Air conditioning
AED 2,082+
Check availability
6 Br 'camp' House On Twin Lakes - Epic Historic Property - Salisbury - Living room
6 Br 'camp' House On Twin Lakes - Epic Historic Property
Salisbury, CT, United States
Air conditioning
AED 2,339+
Check availability
Cottage in the woods - Salisbury - Balcony
Cottage in the woods
Salisbury, CT, United States
9.0Wonderful(1)
Free Wi-Fi
Air conditioning
AED 2,376+
Check availability
Curated Contemporary for lakes, forest & ski hills - Salisbury - Lounge
Curated Contemporary for lakes, forest & ski hills
Salisbury, CT, United States
10Wonderful(4)
Free Wi-Fi
Air conditioning
AED 2,945+
Check availability
Charming 4-bedroom house with AC and WiFi in fabulous Westport - Westport - Dining room
Charming 4-bedroom house with AC and WiFi in fabulous Westport
Westport, CT, United States
Air conditioning
AED 3,834+
Check availability
Main Street Stay Westport - Westport - Living room
Main Street Stay Westport
Westport, CT, United States
9.0Wonderful(2)
Air conditioning
AED 3,863+
Check availability
Beechmont-Charming Colonial for Events and Getaways! - Bridgeport - Building
Beechmont-Charming Colonial for Events and Getaways!
Bridgeport, CT, United States
9.0Wonderful(1)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 4,366+
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 293. The highest prices are found on Wednesday, with average rates at AED 3,991.

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.
Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
July
AED 1,159
AED 1,062
Cheapest month to stay with an average 24% drop in price.
Most expensive month to stay with an average 73% 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 189. 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, 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

Complete your trip to Connecticut

Flights to Connecticut
Car rentals in Connecticut