Connecticut holiday rentals

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Best Connecticut holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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R0 - R19 308R19 308 - R38 598R38 598 - R57 889R57 889 - R77 179R77 179+ per night

Property Types

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Connecticut

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Private Rv - Hartford
Private Rv
Hartford, CT, United States
5.8Fair(12)
Free Wi-Fi
Pet-friendly
Air conditioning
R914+
Check availability
Rock Pad for Yale, Visitors, Nurses, Staff - New Haven
Rock Pad for Yale, Visitors, Nurses, Staff
East Rock
6.2Okay(31)
Parking
Free Wi-Fi
R1 581+
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XL Center 1-Br Condo Dwntn Hartford Easy Parking - Hartford - Bedroom
XL Center 1-Br Condo Dwntn Hartford Easy Parking
Downtown
6.9Okay(25)
Free Wi-Fi
Pet-friendly
Air conditioning
R3 724+
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Experience Downtown Hartford near XL Center - Hartford - Bedroom
Experience Downtown Hartford near XL Center
Downtown
9.0Wonderful(2)
Free Wi-Fi
Air conditioning
R3 953+
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(High Demand)close To Downtown Free Wi-Fi/Parking/ Metro North & I-95 3 Mins - Bridgeport - Bedroom
(High Demand)close To Downtown Free Wi-Fi/Parking/ Metro North & I-95 3 Mins
Bridgeport, CT, United States
Air conditioning
R3 971+
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New Haven Stays - New Haven
New Haven Stays
Downtown
8.9Very Good(120)
Free Wi-Fi
Air conditioning
R4 482+
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Spacious Stay near Yale in Downtown New Haven - New Haven - Living room
Spacious Stay near Yale in Downtown New Haven
Downtown
8.6Very Good(67)
Free Wi-Fi
Air conditioning
R4 690+
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AO Destinations - Wooster Street in Little Italy New Haven - New Haven - Bedroom
AO Destinations - Wooster Street in Little Italy New Haven
Wooster Square
8.6Very Good(10)
Parking
Free Wi-Fi
Air conditioning
R4 744+
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Modern Apartment in Black Rock- - Bridgeport - Living room
Modern Apartment in Black Rock-
Bridgeport, CT, United States
Free Wi-Fi
Pet-friendly
Air conditioning
R6 219+
Check availability
Lordship Charmer Has It All! Comfortable Stay, Accessible, Family Friendly! - Stratford - Bedroom
Lordship Charmer Has It All! Comfortable Stay, Accessible, Family Friendly!
Stratford, CT, United States
Air conditioning
R7 291+
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Serene 3-bedroom duplex in Bridgeport updated floors new appliance - Bridgeport - Kitchen
Serene 3-bedroom duplex in Bridgeport updated floors new appliance
Bridgeport, CT, United States
R7 502+
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Zen, Spacious & Comfy 2 bed, Lux beds - Bridgeport - Kitchen
Zen, Spacious & Comfy 2 bed, Lux beds
Bridgeport, CT, United States
R8 104+
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Spacious&Gracious- 5BR Fam-Friendly near I95&Shops - Fairfield
Spacious&Gracious- 5BR Fam-Friendly near I95&Shops
Fairfield, CT, United States
5.0Fair(1)
Parking
Free Wi-Fi
Air conditioning
R10 278+
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Light filled zen 3BR Penthouse - 7 min to Westport - Weston
Light filled zen 3BR Penthouse - 7 min to Westport
Weston, CT, United States
Parking
Free Wi-Fi
Air conditioning
R11 420+
Check availability
Seaview Ave House-4br/8ppl Retreat - Bridgeport - Dining room
Seaview Ave House-4br/8ppl Retreat
Bridgeport, CT, United States
Air conditioning
R12 210+
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Historic oyster shack. - Westport - Building
Historic oyster shack.
Westport, CT, United States
R80 570+
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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?

Wednesday offers the lowest rates in Connecticut, with an average nightly price of R27 610. The highest prices are found on Friday, with average rates at R134 813.

How early should you book a vacation rental in Connecticut?

Book at least 75 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)

R5 697

Average price (weekend night)

R5 664
Cheapest month to stay with an average 11% drop in price.
Most expensive month to stay with an average 31% 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 February and August.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Connecticut for 9 days.
  • Pool, fireplace, pet friendly, air-conditioned, and hot tub are the most popular holiday rental property amenities in Connecticut
  • Holiday rentals in Connecticut are around 30% 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 Fairfield (75% of total searches to Connecticut). The next most popular destination is New Haven (25%).

  • 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 R905. 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 R1 212 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, cottages, houses, homestays, lodges, villas, agritourism, bungalows, campgrounds, caravans, cabins, chalets, houseboats, luxury tents, treehouses and castles.

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

    There are a number of dog and pet-friendly Connecticut holiday rentals, with around 19% 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

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