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

Charming Farmhouse W/ Pool & Fishing Pond! - Connecticut
No reviews

Charming Farmhouse W/ Pool & Fishing Pond!

house, Bolton
House to rent. Your accommodation will be located in Bolton.
Services and facilities include a swimming pool, an iron and a kitchen. Take advantage of the Free Parking with this accommodation.
Bluestone Cottage | Historic Goshen Retreat With Saltwater Pool, Cozy Charm & Year Round Adventures - Connecticut
No reviews

Bluestone Cottage | Historic Goshen Retreat With Saltwater Pool, Cozy Charm & Year Round Adventures

cottage, Goshen
This historic cottage in Goshen, located near Miranda Vineyard and Mohawk Mountain ski area, offers a comfortable stay with 3 bedrooms and 2 bathrooms for up to 6 guests.
This property features a saltwater swimming pool and a garden, with a fully equipped kitchen including a fridge and dishwasher, and provides parking and internet access.
Guilford Carriage House At Granite Lodge! - Connecticut
No reviews

Guilford Carriage House At Granite Lodge!

house, Guilford
Accommodation. Your accommodation will be based in Guilford.
Services and facilities: a dish washer, air conditioning and a swimming pool.
Blackwoods Old Country Home 5 Bedroom Home By Redawning - Connecticut
No reviews

Blackwoods Old Country Home 5 Bedroom Home By Redawning

house, Woodbury
This Woodbury holiday home is situated within 5km of Glebe House Museum, The Gertrude Jekyll Garden, Hollow Park, and Pilgrim Mall Shopping Centre, offering easy access to local attractions and Southbury Dog Park.
The five-bedroom property sleeps a large family or group, boasting a private garden, swimming pool, barbecue, free Wi-Fi, parking, and essential kitchen appliances including a fridge, washing machine and coffee maker.

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

Comfortable Home Away From Home - Connecticut
No reviews

Comfortable Home Away From Home

house, East Hartford
Holiday house rental. You will be in East Hartford.
Facilities and services include a barbecue, a kitchen and free parking. Take advantage of the terrace in this house in East Hartford.
The Gardners Cottage 1 Mile From Long Island Sound - Pet Friendly - Connecticut
9.8 25 reviews

The Gardners Cottage 1 Mile From Long Island Sound - Pet Friendly

cottage, Clinton
This pet-friendly cottage in Clinton offers convenient access, being a 4-minute drive from Clinton Town Beach and a 3-minute drive from Clinton Crossing Premium Outlets, with marina activities nearby.
This 1-bedroom, 1-bathroom holiday home accommodates up to four guests and features a fully equipped kitchen, complimentary Wi-Fi, air conditioning, on-site laundry, and a garden, with Hammonasset Beach State Park a short drive away.
Luxury Tiny Home | Near Rocky Neck - Connecticut
10 19 reviews

Luxury Tiny Home | Near Rocky Neck

cabin, East Lyme
This secluded lodge is situated in East Lyme, a mere 3 kilometres from Niantic town centre and within easy reach of Rocky Neck State Park and McCook Point Beach.
This family-friendly lodge accommodates up to four guests and features a private wooded garden with a fire pit, a fully equipped kitchen, a luxurious bathroom with heated floors, in-unit laundry, and entertainment including an arcade and WiFi.
702 M² House ∙ 4 Bedrooms ∙ 10 Guests - Connecticut
No reviews

702 M² House ∙ 4 Bedrooms ∙ 10 Guests

house, Stratford
This Stratford, Connecticut oceanfront property boasts breathtaking Long Island Sound views, situated approximately 120 kilometres from New York City and close to local breweries and wineries.
The 693 square metre house offers four bedrooms, five bathrooms, sleeps ten guests, and includes a private pool (seasonal), fully equipped kitchen, and strong Wi-Fi.

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

Private Guest House W/ Deck + Spectacular Views! - Connecticut
10 39 reviews

Private Guest House W/ Deck + Spectacular Views!

cottage, Montville
This charming cottage is situated in Montville, just 4.2km from Nature's Art Village and 4.3km from Dinosaur Place, offering easy access to family-friendly attractions. It has received excellent guest reviews, making it a popular choice for travellers.
The cottage is a comfortable 58 square metre property with one bedroom and one bathroom, accommodating up to four guests. Amenities include a private pool, a fully equipped kitchen, a patio, internet access, and a selection of games.
Classic Red Barn With Game Room And Gym - Connecticut
9.9 59 reviews

Classic Red Barn With Game Room And Gym

farm, Roxbury
This renovated barn, situated in Roxbury, Litchfield County, Connecticut, offers a private retreat near Roxbury's hiking trails and antique shops.
The self-catering property sleeps four in a king-size bed with a day bed and trundle, boasting a fully equipped kitchen, game room with pool and ping pong tables, and a fitness area; a swimming pool and air conditioning are also included.
The Little Villa - 2bed 1bath Private Suite - Connecticut
9.6 9 reviews

The Little Villa - 2bed 1bath Private Suite

house, Bristol
This Bristol property is conveniently located just 7km from Witch’s Dungeon Classic Movie Museum, 9km from Lake Compounce, and 19km from Central Connecticut State University, making it ideal for exploring the surrounding area. The property has received excellent ratings for cleanliness, location, and overall user experience.
This 2-bedroom house, offering 28 square metres of space, comfortably accommodates 6 guests. The house features a fully equipped kitchen, air conditioning, free Wi-Fi, parking, and a garden, perfect for relaxing after a day of exploring.
Beachfront Connecticut Retreat W/ Views! - Connecticut
9.6 40 reviews

Beachfront Connecticut Retreat W/ Views!

house, Milford
This beachfront property in Milford is just a 3-minute walk from Fort Trumbull Beach and a short distance from Silver Sands State Park Beach, offering a prime location for enjoying the local coastline. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 3-bedroom house is ideal for families or groups of friends, with a floor area of 77 square metres and a guest capacity of 7. Amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, a garden, a spa, parking, and towels and bed linen are provided.

Best Connecticut villas and holiday homes with jacuzzi

Peaceful Spa Villa Getaway - Hot Tub - 3 Minutes To Mohegan Sun Casino - Connecticut
10 45 reviews

Peaceful Spa Villa Getaway - Hot Tub - 3 Minutes To Mohegan Sun Casino

house, Norwich
This charming villa is located on the grounds of the Spa at Norwich Inn, just 3 kilometres from Mohegan Sun Casino and Norwich Golf Course, offering a peaceful retreat from the city. Guests have consistently rated this property as excellent, praising its tranquil setting and luxurious amenities.
The villa features one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy access to a range of facilities including a swimming pool, jacuzzi, gym, and a fully equipped kitchen, making it ideal for a relaxing and enjoyable stay.
The Jefferson Guest House - Connecticut
9.6 30 reviews

The Jefferson Guest House

house, Litchfield
The Jefferson Guest House, a self-catering villa in Litchfield, Connecticut, is conveniently located approximately 20-22km from Regina Laudis Abbey, the Witch's Dungeon Classic Movie Museum, and Flanders Nature Center.
This 121 square metre property boasts one bedroom, one bathroom, and can accommodate up to seven guests, offering amenities such as a fully equipped kitchen, bar, free Wi-Fi, private parking, and a terrace; nearby hiking trails and Lake Compounce (27km) provide additional leisure options.
Spacious Woodbury Home W/ Pool + Hot Tub! - Connecticut
No reviews

Spacious Woodbury Home W/ Pool + Hot Tub!

house, Woodbury
This spacious Woodbury property is situated in a peaceful residential area, just 3 kilometres from the Flanders Nature Center and 4.5 kilometres from the Abbey of Regina Laudis. The house is perfect for large families or groups, offering 4 bedrooms, 3 bathrooms and sleeping up to 19 guests across its 309 square metres of living space. This home is equipped with a modern kitchen, a private swimming pool, a hot tub, a tennis court, a garden, and on-site parking.
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.