Villas and Holiday homes in Connecticut

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Connecticut holiday homes
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3009 Villa rentals in Connecticut

Best Connecticut villas and holiday homes with a pool

Among the 3009 accommodations in Connecticut, here are the 4 best villas and holiday homes with a pool

Historic Colonial Pool Walk To Town - Connecticut
10 3 reviews

Historic Colonial Pool Walk To Town

house, Litchfield
This historic colonial house is located in Litchfield, Connecticut, just a short drive from attractions like Witch’s Dungeon Classic Movie Museum (30km) and Lake Compounce (37km).
The property is a 3-bedroom house with a floor area of 260 square metres, comfortably accommodating up to 11 guests. It features a fully equipped kitchen, a private terrace with sea views, a swimming pool, a garden, and parking.
Bluestone Cottage - Connecticut
No reviews

Bluestone Cottage

house, Goshen
This three-bedroom property in Goshen is located 10 kilometres from the airport and 15 kilometres from the train station.
This holiday home accommodates up to 11 guests and features a private swimming pool, a garden, and a fully equipped kitchen with a dishwasher and oven.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Connecticut
No reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

house, Killingworth
This Killingworth holiday home, situated approximately 21 kilometres from Wesleyan University and 24 kilometres from the Goodspeed Opera House, offers a peaceful retreat in Connecticut.
The 189-square-metre property boasts four bedrooms, two bathrooms, sleeps fifteen guests, and includes a private pool, terrace, free Wi-Fi, and a fully equipped kitchen with dishwasher.
Luxe 5,600-sq-ft Estate Waterfront + Pool - Connecticut
No reviews

Luxe 5,600-sq-ft Estate Waterfront + Pool

house, Westbrook
This Westbrook waterfront property is situated 9.6 kilometres from the Goodspeed Opera House and 9.5 kilometres from the Stanton House Museum, with further attractions approximately 43 to 48 kilometres away.
This spacious 511 square metre residence accommodates up to 23 guests across 5 bedrooms and 6 bathrooms, offering amenities such as a swimming pool, air conditioning, a fireplace, and private parking.

Best family friendly Connecticut villas and holiday home

Among the 3009 accommodations in Connecticut, here are the 4 best family friendly villas and holiday homes

Peaceful Wooded Retreat  Quiet Escape, Close To Wolcott Lakes - Connecticut
9.6 8 reviews

Peaceful Wooded Retreat Quiet Escape, Close To Wolcott Lakes

cabin, Waterbury
This Waterbury mountain lodge is conveniently located near the Brass Mill Center and Bristol Commons shopping centres, offering easy access to Whittemore Glen and Black Rock State Parks.
The 203-square-metre (2188 sq ft) three-bedroom property sleeps five, boasting two queen beds and one twin, a fully equipped kitchen with fridge and dishwasher, air conditioning, Wi-Fi, laundry facilities, and ample parking; nearby activities include fishing and horse riding.
200-year-old Farmhouse Is Fitted With All The Comforts Of 21st Century Living... - Connecticut
10 16 reviews

200-year-old Farmhouse Is Fitted With All The Comforts Of 21st Century Living...

farm, East Windsor
This East Windsor farmhouse, situated in Broad Brook, Connecticut, is conveniently located less than 322 kilometres from New York City, offering easy access to the Promenade Shops at Evergreen Walk and Windsor Meadows State Park.
The 223-square-metre property boasts three bedrooms, three bathrooms, and sleeps six guests, featuring a kitchen with fridge, microwave, and dishwasher, plus a terrace, garden, and year-round bonfire facilities.
Luxecompound-hottub Pool Sauna Treehouse Gamebarn - Connecticut
9.8 245 reviews

Luxecompound-hottub Pool Sauna Treehouse Gamebarn

house, Morris
This secluded Morris cottage enjoys excellent proximity to Bantam Lake, approximately 10 kilometres from Mount Tom Ski Area and the White Memorial Conservation Center trails.
The self-catering property offers a fully equipped kitchen, private pool, sauna, and games barn, sleeping a family comfortably with additional features including a three-story treehouse and dedicated parking.
Exquisite Oceanfront Retreat With Pool And Breathtaking Views - Luxurious Sanctuary - Connecticut
No reviews

Exquisite Oceanfront Retreat With Pool And Breathtaking Views - Luxurious Sanctuary

house, Stratford
This oceanfront property in Stratford offers direct access to Long Island Sound, situated approximately 121 kilometres from New York City and conveniently close to local amenities such as breweries, wineries, and shops.
This spacious 465 square metre, three-storey residence accommodates up to 10 guests with four bedrooms and five bathrooms, featuring a fully equipped kitchen, a swimming pool, air conditioning, Wi-Fi, and a billiards room with a bar for entertainment.

Frequently asked questions about villa rentals in Connecticut

  • What are the must-see attractions in Connecticut?

    For iconic Connecticut sights, you've got Mystic Seaport, a living history museum showcasing maritime life; the Mark Twain House & Museum in Hartford, exploring the author's life; and Yale University's stunning campus in New Haven. Don't forget the charming coastal towns like Mystic and Essex.
  • What are the best villa rentals in Connecticut?

    Among the villa rentals in Connecticut, Windy Top Cottage ~ A Romantic "European" Getaway, Villa Signor and Entire House Magical Waterfront Getaway are the most popular ones.

  • Is Connecticut known for mountains, beaches, forests, or other types of landscapes?

    Connecticut offers a diverse range of landscapes. You'll find stretches of beautiful coastline along the Long Island Sound, rolling hills in Litchfield County, and significant forested areas, particularly in the north-west. While there aren't towering mountain ranges, there are hills and mountains offering scenic views, like those in the Litchfield Hills.
  • What are the best villa rentals with a pool in Connecticut?

    Villa Signor, Charming Historic House In Downtown Mystic and Go Jump In The Lake are the best villa rentals with a pool in Connecticut.

  • What are some surprising and hidden attractions in Connecticut?

    Many overlook the charming town of Kent Falls State Park, with its stunning waterfalls and hiking trails. The submarine base in Groton is another fascinating, lesser-known attraction, offering a glimpse into naval history. Also, explore the charming villages and antique shops scattered throughout the Litchfield Hills.
  • What are the best villa rentals with a jacuzzi in Connecticut?

  • What are some unique ways to learn about the culture of Connecticut by engaging with its people?

    Attend a local farmers' market – many towns have them throughout the summer and autumn, offering a chance to chat with producers and learn about regional specialties. Visiting smaller, family-run businesses, like antique shops or local craft stores, allows for interaction with people passionate about their work and the state's heritage. Consider attending a performance at a local theatre or checking out a community event.
  • What are the best villa rentals for families and kids in Connecticut?

  • How much time should you set aside to thoroughly explore Connecticut?

    A week would allow for a good overview of Connecticut's highlights, but to truly explore the state's diverse regions and smaller towns, two weeks or more would be ideal. It depends on your interests and pace, of course.
  • What are the best pet friendly villa rentals in Connecticut?

  • What cultural experiences or workshops in Connecticut offer something different?

    The Mystic Seaport offers workshops on traditional maritime crafts. Many towns host art workshops and classes throughout the year, focusing on local crafts and techniques. Check local listings for specific offerings; availability varies seasonally.
  • What are the best villa rentals with parking in Connecticut?

  • Are there any food festivals in Connecticut where you can try local food?

    Connecticut has many local food events throughout the year. While specific dates vary, the Litchfield County Fair and the Big E (in West Springfield, Massachusetts, close to the Connecticut border) are large-scale events showcasing regional produce and cuisine. Many smaller towns host their own festivals and farmers' markets.
  • What seasonal natural events, such as migrations or blooming periods, occur in Connecticut?

    Autumn brings spectacular foliage changes, particularly in Litchfield County and the northwest hills. Spring sees the blossoming of wildflowers, and bird migrations are noticeable throughout the year, especially along the coast. Check local resources for specific timing of these events, as they vary year to year.
  • What exclusive experiences are available when visiting Connecticut?

    A private tour of the Mark Twain House offers a more intimate look at the author's life and work. A sailing trip along the Long Island Sound provides a unique perspective on the coastline. Many smaller, family-run businesses offer unique experiences, like private cooking classes or guided nature walks. Checking local listings for specific offerings is recommended.

Nearby regions

Best Connecticut villas and holiday homes with a kitchen

Our Cottage - Small In Size, Big In Character, On Beautiful Highland Lake - Connecticut
10 50 reviews

Our Cottage - Small In Size, Big In Character, On Beautiful Highland Lake

cottage, Winchester
This charming cottage is situated in the heart of Winsted, offering easy access to local shops, restaurants, and attractions. It has been consistently rated excellent by previous guests.
The cottage provides comfortable accommodation for up to six guests, with two bedrooms, one bathroom, and a total floor area of 58 square metres. The property comes equipped with a gourmet kitchen, a private dock with waterfront access, and a spacious garden, perfect for enjoying the outdoors.
Morgan · Casa Al Mare Beachfront Retreat Oceanview - Connecticut
9.6 195 reviews

Morgan · Casa Al Mare Beachfront Retreat Oceanview

apartment, East Haven
This charming house is located in Morgan Point, East Haven, just a short 10-minute walk from West Silver Sands Beach and Shell Beach. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The house has four bedrooms and can accommodate up to 12 guests, making it perfect for families or groups of friends. Enjoy a range of amenities including a private garden, barbecue grill, balcony, Jacuzzi, and a fully equipped kitchen.
Lovely Norwich Villa, On Golf Course W/ Amenities! - Connecticut
9.8 14 reviews

Lovely Norwich Villa, On Golf Course W/ Amenities!

house, Norwich
This house is located in Norwich, just a short distance from the Mohegan Sun Casino, Arena, and Norwich Golf Course. The surrounding area offers a mix of entertainment, leisure activities, and historical sites. This property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The house is a spacious one-bedroom property with two bathrooms and can comfortably accommodate up to four guests. It features a fully equipped kitchen, a balcony, a swimming pool, a Jacuzzi, a spa, and parking, making it ideal for a relaxing and enjoyable stay.
Historic Essex Home W/ Large Yard Near Downtown! - Connecticut
9.8 217 reviews

Historic Essex Home W/ Large Yard Near Downtown!

house, Essex
This charming Essex house is situated just 16 kilometres from the Goodspeed Opera House and 34 kilometres from Wesleyan University, offering a peaceful retreat in a quiet neighbourhood close to the town centre. The property has received excellent ratings for location, cleanliness, and overall user experience, making it a popular choice for travellers.
This 2-bedroom property, spanning 130 square metres, comfortably accommodates up to 4 guests. The house features a fully equipped kitchen, a spacious living area, a private garden, a spa, and parking, offering a range of amenities and activities for a relaxing and enjoyable stay.

Best Connecticut villas and holiday homes with jacuzzi

Brand New Cozy Waterfront House W Jacuzzi - Connecticut
No reviews

Brand New Cozy Waterfront House W Jacuzzi

house, New Haven
This New Haven waterfront property is situated 4.5km from Yale University, 3.9km from City Hall, and 6km from Tweed-New Haven Airport.
The one-bedroom, two-bathroom dwelling sleeps six guests and boasts a fully equipped kitchen, jacuzzi, private garden, free Wi-Fi, and on-site parking.
Lovely Norwich Villa, On Golf Course W/ Amenities! - Connecticut
No reviews

Lovely Norwich Villa, On Golf Course W/ Amenities!

house, Norwich
House. Your accommodation will be located in Norwich.
Services and facilities: a dish washer, a jacuzzi and free parking.
Montville Retreat Near Mohegan Sun: 2-home Bundle! - Connecticut
No reviews

Montville Retreat Near Mohegan Sun: 2-home Bundle!

cottage, Montville
This Montville holiday let provides views of Lake Konomoc and is situated opposite a nature preserve, with Mohegan Sun Casino 22.5 kilometres away.
This 142 square metre cottage accommodates six guests and features a private guest house and studio, an indoor hot tub, a seasonal outdoor pool, a pool table and a stone fireplace.
The Goshen Glass Chalet - Connecticut
9.8 208 reviews

The Goshen Glass Chalet

apartment, Goshen
This charming chalet is situated in Goshen, a peaceful lake community just a short drive from Woodridge Lake, offering a tranquil escape surrounded by stunning natural beauty. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The chalet has three bedrooms and two bathrooms, accommodating up to six guests comfortably. You'll enjoy a well-equipped kitchen, a spacious living area with a fireplace, a private garden, a tennis court, and a jacuzzi, making it perfect for relaxing and enjoying the surrounding area.
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