Connecticut holiday rentals

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Best Connecticut holiday rentals

Most recommended holiday rentals in Connecticut

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Orange Oasis in the Heart of East Rock with FREE parking near DT and Yale - New Haven - Kitchen
Orange Oasis in the Heart of East Rock with FREE parking near DT and Yale
East Rock
9.5Wonderful(18)
Parking
Free Wi-Fi
Air conditioning
£290+
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Lake Home - Greenwich - Outdoor view
Lake Home
Greenwich, CT, United States
Parking
Free Wi-Fi
Air conditioning
£135+
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Greenwich Ct. Rye N.Y. 2 Bedroom Loft Apartment!! - Port Chester - Pool
Greenwich Ct. Rye N.Y. 2 Bedroom Loft Apartment!!
Port Chester, NY, United States
8.7Very Good(11)
Air conditioning
£268+
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Villa Spa Blu condo - Norwich - Living room
Villa Spa Blu condo
Norwich, CT, United States
8.5Very Good(1)
Free Wi-Fi
Pool
Air conditioning
£260+
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The Safe House - High Tech Apt #3 - 4 beds - Greenwich - Bedroom
The Safe House - High Tech Apt #3 - 4 beds
Greenwich, CT, United States
Free Wi-Fi
Air conditioning
£181+
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Charming duplex with private yard. Close to the beach, dining & shopping! - Greenwich - Living room
Charming duplex with private yard. Close to the beach, dining & shopping!
Greenwich, CT, United States
9.8Wonderful(11)
Free Wi-Fi
Pet-friendly
Air conditioning
£285+
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Cozy Gem in the Heart of East Rock with FREE Parking near Yale and DT - New Haven - Living room
Cozy Gem in the Heart of East Rock with FREE Parking near Yale and DT
East Rock
8.2Very Good(25)
Parking
Free Wi-Fi
Air conditioning
£268+
Check availability
Luxury Apartments by Hyatus at Pierpont - New Haven - Living room
Luxury Apartments by Hyatus at Pierpont
The Hill
9.5Wonderful(40)
Parking
Free Wi-Fi
Pool
Pet-friendly
£326+
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Econo Lodge Milldale - Southington - Milldale - Building
Econo Lodge Milldale - Southington
Milldale, CT, United States
6.6Okay(382)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£61+
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Rowayton House Close To Town - Norwalk - Outdoor view
Rowayton House Close To Town
Norwalk, CT, United States
Free Wi-Fi
Pet-friendly
Air conditioning
£832+
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Your perfect Westport getaway is here! - Westport - Balcony
Your perfect Westport getaway is here!
Westport, CT, United States
£207+
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Luxury Villa- 3 mins to Mohegan- Fully Stocked with Fireplace- Jacuzzi, Saltwater Pools, Sauna - Norwich - Living room
Luxury Villa- 3 mins to Mohegan- Fully Stocked with Fireplace- Jacuzzi, Saltwater Pools, Sauna
Norwich, CT, United States
8.9Very Good(23)
Parking
Free Wi-Fi
Pool
Air conditioning
£245+
Check availability
California guest house - Greenwich
California guest house
Greenwich, CT, United States
10Wonderful(1)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£196+
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Humble Beginnings - Norwich
Humble Beginnings
Norwich, CT, United States
8.0Very Good(1)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£115+
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Homestay in Norwalk near St. Ladislaus Church - Norwalk
Homestay in Norwalk near St. Ladislaus Church
Norwalk, CT, United States
£64+
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Cozy Villa 3 mins to Mohegan- Fully Stocked with King Bed & Fireplace- Jacuzzi, Saltwater Pools, Sauna - Norwich
Cozy Villa 3 mins to Mohegan- Fully Stocked with King Bed & Fireplace- Jacuzzi, Saltwater Pools, Sauna
Norwich, CT, United States
9.2Wonderful(13)
Parking
Free Wi-Fi
Pool
Air conditioning
£234+
Check availability
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£23 - £230£230 - £436£436 - £641£641 - £847£847+ per night

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Free cancellationFree breakfastFree parkingFree internet

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 August, with average rates of £34. In comparison, June is the most expensive month, with prices at £137.

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

Monday offers the lowest rates in Connecticut, with an average nightly price of £31. The highest prices are found on Friday, with average rates at £82.

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

August

Average price (weeknight)

£179

Average price (weekend night)

£199
Cheapest month to stay with an average 26% drop in price.
Most expensive month to stay with an average 108% 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 March and May.
  • The cheapest night for renting a holiday home in Connecticut is Friday. In contrast, the most expensive is Thursday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Connecticut for 3 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 28% more expensive than hotels on average. Search here to compare prices for all accommodation types in Connecticut.
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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 Hartford (36% of total searches to Connecticut). The next most popular destinations are New Haven (18%) and Norwich (18%). Searches for holida rentals in Stamford (9%), Farmington (9%) and Milford (9%) 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 £38. 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, cottages, houses, homestays, lodges, condos, villas, agritourism, caravans, cabins, chalets, houseboats, barns, luxury tents, treehouses, bungalows and castles.

  • What are some of the most-loved holiday rentals available in Connecticut?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Econo Lodge.

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

    There are a number of dog and pet-friendly Connecticut holiday rentals, with around 18% allowing you to bring your pet along with you.

See more FAQs

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

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