Connecticut vacation rentals

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Best Connecticut vacation rentals

Most recommended vacation rentals in Connecticut

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Cozy Bridgeport Apartment 2 Mi to Downtown! - Bridgeport - Living room
Cozy Bridgeport Apartment 2 Mi to Downtown!
5 Fair
566 ﷼+
566 ﷼+
Free Wi-Fi
Air Conditioning
Secluded 2-acre Lake Front Home! Special off-season rates! - Woodstock - Building
Secluded 2-acre Lake Front Home! Special off-season rates!
2,482 ﷼+
2,482 ﷼+
Free Wi-Fi
Air Conditioning
Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!! - Woodstock - Bedroom
Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!! - Woodstock - Bedroom
Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!!
2,024 ﷼+
2,024 ﷼+
Air Conditioning
The Blue Sapphire 2BR 2 King beds & ample backyard - Bridgeport - Bedroom
The Blue Sapphire 2BR 2 King beds & ample backyard - Bridgeport - Bedroom
The Blue Sapphire 2BR 2 King beds & ample backyard
9.2 Wonderful
993 ﷼+
993 ﷼+
Parking
Free Wi-Fi
Air Conditioning
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway! - Woodstock - Patio
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway! - Woodstock - Patio
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!
2,500 ﷼+
2,500 ﷼+
Free Wi-Fi
Air Conditioning
Walk To Goodspeed Opera House! - East Haddam - Kitchen
Walk To Goodspeed Opera House! - East Haddam - Kitchen
Walk To Goodspeed Opera House!
10 Wonderful
813 ﷼+
813 ﷼+
Air Conditioning
Luke's Landing - Westport - Bedroom
Luke's Landing - Westport - Bedroom
Luke's Landing
1,796 ﷼+
1,796 ﷼+
Parking
Free Wi-Fi
Air Conditioning
Main Street Stay Westport - Westport - Living room
Main Street Stay Westport - Westport - Living room
Main Street Stay Westport
2,474 ﷼+
2,474 ﷼+
Parking
Free Wi-Fi
Air Conditioning
Pet-Friendly Getaway in Historic East Haddam Home\n\n - East Haddam - Bedroom
Pet-Friendly Getaway in Historic East Haddam Home\n\n - East Haddam - Bedroom
Pet-Friendly Getaway in Historic East Haddam Home\n\n
1,559 ﷼+
1,559 ﷼+
Air Conditioning
Quiet Cozy Stay Spacious Home Near Beach & Shops - Hamden - Patio
Quiet Cozy Stay Spacious Home Near Beach & Shops - Hamden - Patio
Quiet Cozy Stay Spacious Home Near Beach & Shops
8 Very good
2,023 ﷼+
2,023 ﷼+
Parking
Free Wi-Fi
Air Conditioning
Modern Westport Studio with Pool Table & Lounge - Westport - Living room
Modern Westport Studio with Pool Table & Lounge - Westport - Living room
Modern Westport Studio with Pool Table & Lounge
8.5 Very good
802 ﷼+
802 ﷼+
Parking
Free Wi-Fi
Air Conditioning
The B&W Haven 3BR private office by LI Ferry - Bridgeport - Bedroom
The B&W Haven 3BR private office by LI Ferry - Bridgeport - Bedroom
The B&W Haven 3BR private office by LI Ferry
8.7 Very good
1,237 ﷼+
1,237 ﷼+
Parking
Free Wi-Fi
Air Conditioning
Charming Colonial for Events and Getaways! - Bridgeport - Building
Charming Colonial for Events and Getaways! - Bridgeport - Building
Charming Colonial for Events and Getaways!
1,732 ﷼+
1,732 ﷼+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
Private Sandy Beach Amazing Waterfront & Hot Tub - Branford - Bathroom
Private Sandy Beach Amazing Waterfront & Hot Tub - Branford - Bathroom
Private Sandy Beach Amazing Waterfront & Hot Tub
9.5 Wonderful
5,837 ﷼+
5,837 ﷼+
Parking
Free Wi-Fi
Air Conditioning
Connecticut Lake House - Bridgeport
Connecticut Lake House - Bridgeport
Connecticut Lake House
5.1 Fair
615 ﷼+
615 ﷼+
Parking
Free Wi-Fi
Air Conditioning
Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt - East Haddam
Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt - East Haddam
Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt
9.2 Wonderful
851 ﷼+
851 ﷼+
Parking
Air Conditioning
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0 ﷼ - 4,142 ﷼4,142 ﷼ - 8,284 ﷼8,284 ﷼ - 12,427 ﷼12,427 ﷼ - 16,569 ﷼16,569 ﷼+ per night

Property Types

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Free cancellationFree breakfastFree parkingFree internet

KAYAK’s insights for vacation 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 1,028 ﷼. In comparison, June is the most expensive month, with prices at 3,748 ﷼.

What is the cheapest day of the week to book a vacation rental in Connecticut?

Friday offers the lowest rates in Connecticut, with an average nightly price of 1,465 ﷼. The highest prices are found on Saturday, with average rates at 2,102 ﷼.

How early should you book a vacation rental in Connecticut?

Book at least 51 days before your stay begins to get the best price for your Connecticut vacation rental.
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Good to know

Low season

January

High season

July

Average price (weeknight)

1,053 ﷼

Average price (weekend night)

1,497 ﷼
Cheapest month to stay with an average 11% drop in price.
Most expensive month to stay with an average 32% 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 vacation rental

FAQs when booking a vacation home in Connecticut

  • How much is a vacation rental in Connecticut for tonight?

    In the last 72 hours, users have found Connecticut vacation rentals for tonight for as low as 362 ﷼. Search here for similar prices

  • What types of vacation rentals are available in Connecticut?

    There are loads of different property types that you can make your vacation home in Connecticut. You’ll find apartments, condos, cottages, houses, homestays, lodges, villas, bungalows, caravans, agritourism, cabins, chalets, houseboats, luxury tents, treehouses and castles.

  • Are there any pet-friendly vacation rentals in Connecticut?

    There are a number of dog and pet-friendly Connecticut vacation rentals, with around 18% 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 vacation home.

Everything you need to know for your stay in Connecticut

Complete your trip to Connecticut

Car rentals in Connecticut

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