Holiday Rentals in Connecticut

17164 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 17164 accommodations in Connecticut, here are the 4 best family friendly rentals

Cozy 3-bedroom Cabin In Woodbury. With Brook And Mountain To Enjoy. - Connecticut
9.8 8 reviews

Cozy 3-bedroom Cabin In Woodbury. With Brook And Mountain To Enjoy.

cabin, Woodbury
This 93 square meter, three-bedroom lodge in Woodbury offers proximity to Flanders Nature Centre and Steep Rock Preserve, as well as historical sites including Hollister House Garden and Bellamy-Ferriday House and Garden.
This family-friendly accommodation provides WiFi, air conditioning, a microwave, and parking for up to six guests, with nearby opportunities for game walks and birdwatching.
Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc - Connecticut
9.2 4 reviews

Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc

house, Fairfield
This charming cottage is located in Fairfield, just 18 kilometres from Silver Sands State Park, 22 kilometres from Connecticut Post Mall Shopping Centre, and 32 kilometres from The Yale Bowl, offering a peaceful retreat away from the hustle and bustle. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The cottage features three bedrooms and one bathroom, spanning 130 square metres and comfortably accommodating up to six guests. It boasts a fully equipped kitchen, private patio, air conditioning, complimentary Wi-Fi, and private parking, along with a garden and outdoor play equipment for families.
Waterfront Retreat Private Beach + Hottub Sunsets - Connecticut
9.9 166 reviews

Waterfront Retreat Private Beach + Hottub Sunsets

apartment, Branford
This beachfront holiday home is located in Branford's city centre, just a short distance from Stony Creek Brewery and within easy reach of Double Beach and Polished. The property has consistently received excellent ratings for user experience, location, and cleanliness.
This spacious four-bedroom property offers 297 square metres of living space. The house is equipped with a range of amenities, including a fully equipped kitchen, a Jacuzzi, a fitness centre, a tennis court, and a garden.
Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy - Connecticut
10 4 reviews

Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy

house, Bethlehem
This Bethlehem holiday home, located near the Abbey of Regina Laudis (3.4km) and Flanders Nature Centre (4.7km), offers a peaceful woodland retreat.
The 171 square metre property boasts one bedroom, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen, spa, terrace, garden, free Wi-Fi, parking, and outdoor play equipment.

Top cities

Best pet friendly Connecticut holiday rentals

Among the 17164 accommodations in Connecticut, here are the 4 best pet friendly rentals

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min - Connecticut
9.6 12 reviews

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

apartment, Bridgeport
This pet-friendly apartment in Bridgeport's Downtown district is conveniently located less than 0.8 km from Bridgeport Train Station and within walking distance of the Baldwin Plaza Shopping Centre.
The one-bedroom flat sleeps two guests and includes amenities such as free Wi-Fi, a smart TV, and on-site parking, with easy access to attractions like the Barnum Museum and Beardsley Zoo.
The Connecticut Cottage Historic Modern Charm - Connecticut
10 3 reviews

The Connecticut Cottage Historic Modern Charm

cottage, Clinton
This 1790s stone holiday home in Clinton offers a prime shoreline position, located 5 minutes' drive from Clinton Outlets and Town Beach, and 10-15 minutes' drive from Madison Beaches and Old Saybrook Historic Downtown.
This two-bedroom, two-bathroom holiday home accommodates up to four guests and features air conditioning, Wi-Fi, a garden, and parking, with nearby attractions including the Allis-Bushnell House and Museum and the Hyland House Museum.
2 Queen Beds  Suite Non-smoking Micfridge - Connecticut
No reviews

2 Queen Beds Suite Non-smoking Micfridge

apartment, Enfield
This Enfield flat offers convenient access just off I-91, situated 500 metres from Brookside Plaza and a short drive to Bradley International Airport.
This ground floor suite accommodates four guests with two Queen Beds, featuring air conditioning, Wi-Fi, cable TV, a microwave, fridge, and an on-site coin laundry facility.
1 King Bed  Non-smoking - Connecticut
No reviews

1 King Bed Non-smoking

apartment, Milford
This studio flat in Milford is located 3 kilometres from Walnut Beach and Silver Sands State Park Beach, and 26 kilometres from Tweed-New Haven Airport.
This 19 square metre studio apartment accommodates two guests and features air conditioning, complimentary WiFi, an outdoor swimming pool, and parking, with a 24-hour front desk available.

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 17164 accommodations in Connecticut, here are the 4 best rentals with a pool

Secluded Farmhouse On 14 Private Acres - Connecticut
9.9 40 reviews

Secluded Farmhouse On 14 Private Acres

apartment, Goshen
This Goshen farmhouse, situated near Litchfield, Connecticut, offers easy access to Mohawk Mountain and other ski resorts, being approximately 160km from New York City.
This 14-acre estate boasts a 4-bedroom, 3-bathroom property sleeping up to 10 guests, featuring a 50ft pool, cinema room, multiple living areas, a fully equipped kitchen with high-end appliances, and fast Wi-Fi.
Historic Inn On A 100 Acre Organic Farm With Lake, Private Pool & Gourmet Food - Connecticut
10 119 reviews

Historic Inn On A 100 Acre Organic Farm With Lake, Private Pool & Gourmet Food

apartment, East Lyme
This family-friendly house is located in East Lyme, just 5km from Flanders Plaza Shopping Centre and Cedar Ridge Golf Course, offering a peaceful and convenient base for exploring the area. The property has received excellent user reviews, highlighting its comfortable and well-equipped nature.
This spacious 7-bedroom house can comfortably accommodate up to 14 guests, providing ample space for families or groups of friends. Guests can enjoy a range of amenities including a private pool, a spa, a garden, a terrace, and a fully equipped kitchen, making it ideal for a relaxing and enjoyable stay.
Sunny Modern 3 Bedroom House Walk To  Beach And Town - Connecticut
No reviews

Sunny Modern 3 Bedroom House Walk To Beach And Town

apartment, Fairfield
This three-bedroom flat is located in Downtown Fairfield, a 14-minute walk from the Fairfield Museum and History Centre and a 10-minute walk from South Benson Marina.
This apartment offers accommodation for six guests with air conditioning, a hot tub, on-site laundry facilities, and essential toiletries.
Akasa Ocean Front Oasis- Seasonal Pool, Grill - Connecticut
10 15 reviews

Akasa Ocean Front Oasis- Seasonal Pool, Grill

apartment, Stratford
This luxurious Stratford apartment, located in the Lordship neighbourhood, offers direct beach access and is close to attractions such as the National Helicopter Museum and Beardsley Zoo.
The 702-square-metre property boasts four bedrooms, five bathrooms, a private pool with ocean views, and can comfortably accommodate ten guests, along with amenities including a fully equipped kitchen, air conditioning, and parking.

Best Connecticut holiday rentals with parking

2 Br In Yale Campus, Very Safe Area, Free Parking - Connecticut
9.8 42 reviews

2 Br In Yale Campus, Very Safe Area, Free Parking

apartment, New Haven
This flat offers a prime location within Yale University, adjacent to Yale Science Hill and a 10-minute walk from Old Campus and downtown New Haven.
This property accommodates up to six guests across two bedrooms and a sofa bed in the living room, featuring a well-equipped kitchen, air conditioning, and complimentary parking.
Sunny 1 Full Bed Ada|free Parking - Connecticut
No reviews

Sunny 1 Full Bed Ada|free Parking

apartment, Milford
This apartment in Milford is situated on a lake, offering convenient access within a short drive to Silver Sands State Park, the Housatonic Museum of Art, and the Barnum Museum.
This 19 square metre flat accommodates two guests and features air conditioning, high-speed internet, free parking, and access to an outdoor swimming pool and fitness centre.
Modern Apartment In Black Rock - Connecticut
9.6 17 reviews

Modern Apartment In Black Rock

apartment, Bridgeport
This beachfront apartment in Bridgeport, Connecticut is conveniently located less than 1.6km from Longfellow and Seaside Parks, and under 4.8km from Fairfield Museum and History Centre and Fairfield University.
The 83 square metre flat offers one bedroom, one bathroom, sleeps three, and includes a fully equipped kitchen, in-unit laundry, and a sofa bed; nearby attractions include Fairfield Metro Station, a 17-minute walk away.
Private Beach Cottage In Point O'woods - Connecticut
9.6 272 reviews

Private Beach Cottage In Point O'woods

apartment, Old Lyme
This charming cottage is situated in the private, gated community of Point O'Woods Beach in Old Lyme, just a short walk from the beach and within a 24-40 kilometre drive of Mohegan Sun Casino, Mystic Seaport, and Essex. The cottage has received excellent ratings for its location, cleanliness, and overall user experience.
The cottage has one bedroom and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including air conditioning, a hot tub, a grill, a fire pit, an indoor fireplace, a washer/dryer, a private deck, and access to community amenities such as tennis courts, a playground, a basketball court, a bocce court, and a boat launch.
©2026 cozycozy.com