Holiday Rentals in Connecticut

11702 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Connecticut holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Connecticut

Best family friendly Connecticut holiday rentals

Among the 11702 accommodations in Connecticut, here are the 4 best family friendly rentals

4 Bedroom Home Tucked Away In Litchfield Hills - Connecticut
10 52 reviews
Connecticut
20/08 – 22/08
SG$801/nighttotal: SG$1602 (2 )

4 Bedroom Home Tucked Away In Litchfield Hills

5 6
apartment , Litchfield
This five-bedroom apartment is located in Litchfield, just a short distance from the town centre and within easy reach of the Litchfield Historical Society and the Litchfield Green. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spread over three floors and can comfortably accommodate nine guests. It features a fully equipped kitchen, multiple bathrooms, a dedicated play area, and a separate reading room.
Studio Flat Above Historic Cider Mill - Connecticut
9.9 364 reviews
Connecticut
21/08 – 23/08
SG$488/nighttotal: SG$976 (2 )

Studio Flat Above Historic Cider Mill

1 3
studio , Westport
This Westport apartment is conveniently located within a 3-mile radius of Southport Beach, Burying Hill Beach, and the Country Club of Fairfield, making it ideal for exploring the area. It has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment offers a spacious 79 square metre layout with one bedroom and one bathroom, comfortably accommodating up to four guests. It is fully equipped with a kitchen, laundry facilities, air conditioning, a jacuzzi, and parking, as well as free Wi-Fi, a Smart TV, and a coffee/tea maker for a relaxing and convenient stay.
Farm - Animals - Barn - Gazebo - Fire Pit - 2xking - Connecticut
9.8 524 reviews
Connecticut
23/07 – 25/07
SG$396/nighttotal: SG$792 (2 )

Farm - Animals - Barn - Gazebo - Fire Pit - 2xking

2 2
apartment , Willington
This two-bedroom flat is located in a rural setting in Willington, Connecticut, just 14 kilometres from Tinkerville Brook Reserve, the University of Connecticut, and the William Benton Museum of Art. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The flat features a well-equipped kitchen, a comfortable living area with a fireplace, and a private balcony. Guests can enjoy the on-site garden, barbecue facilities, and parking, as well as access to a range of amenities including air conditioning, internet, and a DVD player.
87 M² House ∙ 1 Bedroom ∙ 2 Guests - Connecticut
Connecticut
10/07 – 09/08
SG$143/nighttotal: SG$4290 (30 )

87 M² House ∙ 1 Bedroom ∙ 2 Guests

1 2
house , Wallingford
House to rent for 2 guests. Your accommodation will be based in Wallingford.
Services and facilities: air conditioning, a freeze and free parking. This house also has a garden!

Top cities

Best pet friendly Connecticut holiday rentals

Among the 11702 accommodations in Connecticut, here are the 4 best pet friendly rentals

2 Bedroom Boathouse - Connecticut
9.6 30 reviews
Connecticut
27/06 – 28/06
SG$463/nightfor 1 night

2 Bedroom Boathouse

1 2
barge , Milford
This unique floating accommodation is located in the Dockside marina on the Housatonic River in Milford, just a short distance from the historic downtown area and its charming shops and restaurants. The marina offers a tranquil setting, perfect for a relaxing break.
This barge has two bedrooms and one bathroom and can accommodate up to eight guests. Guests can enjoy a spacious living area with a pull-out couch, a kitchenette, and a master suite with a queen bed and a single-sleeper couch, as well as a lower cabin with two twin beds. Amenities include air conditioning, internet access, parking, and three outdoor decks with spectacular views of the Housatonic River.
Dtwn Yale Wooster Square Laundry - Connecticut
9.2 5 reviews
Connecticut
26/06 – 29/06
SG$509/nighttotal: SG$1527 (3 )

Dtwn Yale Wooster Square Laundry

1 4
apartment , New Haven
This New Haven apartment, situated in the Wooster Square neighbourhood, is a short walk from City Hall and a 3 km stroll from Yale University.
The one-bedroom flat, sleeping up to nine guests, offers a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, air conditioning, parking, and is close to the Yale Bowl and Tweed-New Haven Airport.
Landing | Stylish 1bd, Gym, Game Room - Connecticut
8.2 10 reviews
Connecticut
19/07 – 19/08
SG$136/nighttotal: SG$4216 (31 )

Landing | Stylish 1bd, Gym, Game Room

1 1
apartment , Hartford
This studio apartment at The Millennium in Hartford, CT, offers easy access to I-84 and I-91, placing you minutes from downtown Hartford's theatre and dining districts, Bushnell Park, Dunkin' Park, and the Connecticut Science Center.
This fully furnished flat accommodates two guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, complimentary internet, and in-unit laundry, with secure building access, private garage parking, and river views.
Cozy 2-bedroom Apartment In Charming New Britain With Wifi - Connecticut
Connecticut
02/07 – 06/07
SG$248/nighttotal: SG$992 (4 )

Cozy 2-bedroom Apartment In Charming New Britain With Wifi

2 2
apartment , New Britain
This New Britain apartment, conveniently located near the Hill-Stead Museum and Stanley-Whitman House, offers easy access to local attractions.
The two-bedroom, one-bathroom flat sleeps four guests comfortably, featuring queen-sized beds, in-unit laundry, Wi-Fi, air conditioning, and is close to Dinosaur State Park and the XL Center.

Frequently asked questions about holiday rentals in Connecticut

  • What are the must-see sights in Connecticut, United States?

    Mystic Seaport Museum, a living history museum showcasing maritime life; Mark Twain House & Museum, the preserved home of the famous author; Yale University in New Haven, a stunning campus with historical buildings; and the charming coastal towns of Mystic and Essex are all popular choices.
  • What are the best Airbnb and vacation rentals in Connecticut?

    Whole Apartment - Private - Walk To Yale And Downtown, Windy Top Cottage ~ A Romantic "European" Getaway and Villa Signor are the most popular Airbnb and vacation rentals in Connecticut among travelers.

  • What hotel options are available in Connecticut?

    You can find luxury hotels overlooking a harbor, budget motels, study hotels in Yale, humble inns, as well as cozy bed and breakfasts in historic houses in Connecticut. We can help you find the right hotel for you in Connecticut in just seconds and at the best price.
  • Are there any unique natural phenomena in Connecticut, United States?

    While Connecticut doesn't have dramatic geological features like massive canyons, its coastline offers beautiful rocky shores and sandy beaches. The state also boasts numerous state parks with diverse ecosystems, including forests and wetlands. Talcott Mountain State Park offers stunning views from Heublein Tower.
  • What are the most popular Airbnbs in Connecticut?

  • Where is the best town to book a hotel in Connecticut?

    Although Stamford, Windsor Locks, and Groton are some of the more popular destinations for travelers visiting Connecticut, you may want to consider some of the smaller, more picturesque towns to visit. Connecticut is not a big state, so anywhere you find pleasant would make a good base. Perhaps consider Essex, Cornwall, Mystic, or Greenwich for somewhere picturesque and peaceful to stay. Of course, if you want somewhere bigger, you can always rub shoulders with the Ivy League crowd in New Haven or head to the state capital of Hartford.
  • What essentials should you bring along to Connecticut, United States?

    Comfortable walking shoes are a must, as are layers of clothing, as the weather can be changeable. Sunscreen and insect repellent are also advisable, especially during warmer months. Don't forget a reusable water bottle, as staying hydrated is important.
  • What are the best vacation rentals with a pool in Connecticut?

    Villa Signor, Charming Historic House In Downtown Mystic and Quiet 2 Bed Room Apt W/ Private Entrance are the best vacation rentals with a pool in Connecticut.

  • Where should you book a hotel for the International Festival of Arts and Ideas?

    The International Festival of Arts and Ideas takes place in New Haven, so you'll want to book your Connecticut hotel here. But make sure you book your hotel in advance.
  • What famous events or festivals are happening in Connecticut, United States?

    The annual Connecticut Renaissance Faire is a popular event, offering a taste of medieval times. Many towns and cities host smaller festivals throughout the year, often celebrating local produce or arts and crafts. Check local listings for specific dates and events.
  • What are the best rentals for families and kids in Connecticut?

  • What is there to do in Connecticut?

    For some history, head to Mystic Seaport, which is home to one of the United State's most prominent maritime museums. Also, don't miss the Yale University Museums, like the Yale Art Gallery or the Peabody Museum of Natural History. Animal lovers may want to come face-to-face with marine life in the Mystic Aquarium, while literature lovers will want to make a pilgrimage to the Mark Twain House and Museum. Of course, you can also just relax by the sea, drive through quaint and pretty villages and enjoy Connecticut life.
  • Where can you find the best restaurants serving local dishes in Connecticut, United States, and what are the must-try specialties?

    Many excellent restaurants across the state serve fresh, locally sourced seafood. Look for restaurants in coastal towns like Mystic and Stonington for the freshest catches. Steamed clams, lobster rolls, and New England clam chowder are must-try specialties.
  • What are the best rentals or Airbnbs with a jacuzzi in Connecticut?

    The best vacation rentals or Airbnb with a jacuzzi in Connecticut are Whole Apartment - Private - Walk To Yale And Downtown, Villa Signor and Spacious 2 Bedroom Apartment Close To Yale Bowl.

  • How can you get around in Connecticut?

    You can get around Connecticut by car easily, as the highways are easy to navigate and plentiful. You can travel by train if you are going along the coast, and there are also services between New Haven and Hartford. In addition, you can get a ferry from Long Island to Connecticut ports. There are also Greyhound buses and buses operated by other companies, like Peter Pan Bus lines.
  • What are some less-famous attractions in Connecticut, United States that are worth a visit?

    The Florence Griswold Museum in Old Lyme, showcasing American Impressionist art; the charming town of Litchfield, with its historic architecture and quaint shops; and hiking trails in the Litchfield Hills offer a more off-the-beaten-path experience.
  • What are the best activities for engaging with locals and understanding their culture in Connecticut, United States?

    Visiting local farmers' markets, attending community events in smaller towns, and striking up conversations with people in local pubs or cafes are great ways to connect with the local culture. Exploring the state's many historical sites can also provide insights into Connecticut's past.
  • What unique natural landscapes and terrain features can travellers explore in Connecticut, United States?

    Connecticut offers a variety of landscapes, from its rocky coastline and sandy beaches to rolling hills and forests in the Litchfield Hills. The state also has several rivers and lakes, perfect for kayaking or canoeing. The diverse terrain provides opportunities for hiking, biking, and other outdoor activities.
  • How many days are ideal for visiting Connecticut, United States, and what are some itinerary suggestions?

    A long weekend (3-4 days) allows for a taste of Connecticut's highlights, focusing on a specific region like the coast or the Litchfield Hills. A week-long trip offers more time to explore different areas and engage in more activities. Possible itineraries could focus on coastal exploration, a historical tour, or a nature-focused trip.

Nearby regions

Best Connecticut holiday rentals with a pool

Among the 11702 accommodations in Connecticut, here are the 4 best rentals with a pool

Villa Mariana Blackberry River. Luxury, Pool, Comfort, Peaceful Nature, Updated - Connecticut
10 15 reviews
Connecticut
16/08 – 20/08
SG$1327/nighttotal: SG$5308 (4 )

Villa Mariana Blackberry River. Luxury, Pool, Comfort, Peaceful Nature, Updated

4 4
apartment , North Canaan
This North Canaan riverfront property is located within a 15-minute walk of the Edith Scoville Memorial Sanctuary and Lawrence Field, and under 2km from the Connecticut Railroad Historical Museum and Douglas Library.
This 326 square metre house boasts four bedrooms, three bathrooms, sleeps eleven guests, and includes a private pool, garden, terrace, free Wi-Fi, and a fully equipped kitchen.
Studio Available - Pool/gym/laundry - Connecticut
10 1 review
Connecticut
24/06 – 30/06
SG$178/nighttotal: SG$1068 (6 )

Studio Available - Pool/gym/laundry

1 2
apartment , Meriden
This studio flat is located in a prime Meriden district, placing you within easy reach of local attractions and city amenities.
This modern studio offers a fully equipped all-electric kitchen, air conditioning, internet, and parking, with swimming pool and fitness centre access, ideal for up to two guests.
Historic 6-bdrm Tudor Estate W Pool/tennis Access - Connecticut
9.6 10 reviews
Connecticut
27/06 – 04/07
SG$2486/nighttotal: SG$17402 (7 )

Historic 6-bdrm Tudor Estate W Pool/tennis Access

6 9
apartment , Stamford
This six-bedroom apartment is ideally located in central Stamford, just a short walk from both E. Gaynor Brennan Golf Course and Stamford Hospital. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious flat is perfect for large groups or families, offering a comfortable and well-equipped living space. Guests can enjoy a range of amenities, including a swimming pool, tennis court, sauna, and barbecue facilities, as well as a fully-equipped kitchen, a terrace, and a garden.
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Connecticut
Connecticut
30/06 – 15/07
SG$1935/nighttotal: SG$29025 (15 )

Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.

4 2
houseboat , Clinton
This houseboat is situated in Clinton, Connecticut, offering convenient access to RJ Julia Booksellers, located just 300 meters away, and is within easy reach of Clinton Crossing Premium Outlets and Clinton Plaza Shopping Center.
This four-bedroom, four-bathroom vessel accommodates up to eight guests, featuring a king bed, queen bed, and two twin beds, complete with air conditioning and internet, and boasts a flybridge bar and aft deck dining area for enjoying panoramic views.

Best Connecticut holiday rentals with parking

1 Bdr Oasis|10 Mile To Uconn|500mbs|w/d|dishwasher - Connecticut
10 30 reviews
Connecticut
19/07 – 19/08
SG$196/nighttotal: SG$6076 (31 )

1 Bdr Oasis|10 Mile To Uconn|500mbs|w/d|dishwasher

1 1
apartment , Andover
This Andover apartment, a self-contained flat above an attached garage, is situated approximately 24km from the University of Connecticut, 24km from Manchester, and 24km from Willimantic, offering easy access to major Connecticut attractions.
The one-bedroom, one-bathroom property sleeps up to four guests comfortably, includes a fully equipped kitchen with dishwasher, in-unit laundry, designated parking, and is close to walking trails.
Charming Luxury 1br Near Downtown. Dog Friendly! - Connecticut
9.4 13 reviews
Connecticut
02/07 – 06/07
SG$249/nighttotal: SG$996 (4 )

Charming Luxury 1br Near Downtown. Dog Friendly!

1 2
apartment , Manchester
This Manchester apartment is conveniently located within 1.6km of Charter Oak Park and Manchester Memorial Hospital, and within 4.8km of the Lutz Children's Museum and Manchester Parkade.
This self-catering flat offers 42 square metres of space, sleeping up to 3 guests in one bedroom and one bathroom, and includes amenities such as Wi-Fi, air conditioning, on-site parking, a spa, and in-unit laundry facilities.
\Nwhispering Estate  A Romantic Countryside Escape - Connecticut
Connecticut
27/06 – 04/07
SG$19577/nighttotal: SG$137039 (7 )

\Nwhispering Estate A Romantic Countryside Escape

4 9
apartment , Goshen
This country estate in Goshen, Litchfield County, offers secluded accommodation near the Goshen Historic District and West Cornwall Covered Bridge, with the nearest landmark being the covered bridge at approximately 3.5 kilometers away.
This 4-bedroom, 5-bathroom property accommodates up to 12 guests and includes a separate 2-bedroom guesthouse, a 'party barn', a media room, wine cellar, fitness suite, sauna, and game area on 70 acres with a pond and stream.
Entire Apartment Recently Renovated 2br - Connecticut
9.4 209 reviews
Connecticut
27/07 – 07/08
SG$442/nighttotal: SG$4862 (11 )

Entire Apartment Recently Renovated 2br

2 5
apartment , Ansonia
This two-bedroom flat in Ansonia is situated just 2.1 kilometres from the Ansonia Mall Shopping Centre and 4.2 kilometres from the Housatonic River. The self-catering apartment comes with a fully equipped kitchen, a private garden, and on-site parking.
©2026 cozycozy.com