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Kent, CT vacation rentals
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Best Vacation rentals and Airbnb offers in Kent, CT

Choose the Right Family-Friendly Vacation Rentals in Kent, CT

These family-friendly vacation rentals in Kent, CT offer spacious layouts and easy access to top city attractions.

Private New House On 10 Acres Of Pristine Nature - Kent, CT
10 216 reviews
Kent, CT
08/01 – 08/03
$337/nighttotal: $674 (2 )

Private New House On 10 Acres Of Pristine Nature

3 2
apartment , Warren
This charming home in Warren is surrounded by nature and a picturesque pond, within walking distance to restaurants, galleries, and shops. With excellent ratings for location, cleanliness, and user experience, this accommodation is highly recommended for travelers seeking a comfortable and convenient stay.
The home features 3 bedrooms, 2 bathrooms, and a guest capacity of 6. The fully equipped kitchen, inviting living spaces, and laundry room provide added convenience. Guests can enjoy the secluded location with sprawling front and back yards, a fitness center, and a dedicated workout area on the third floor.
Bright And Spacious 3-bedroom House. - Kent, CT
9.0 6 reviews
Kent, CT
08/01 – 08/03
$400/nighttotal: $800 (2 )

Bright And Spacious 3-bedroom House.

1 2
apartment , Kent
This comfortable 3-bedroom house is located in a rural setting in Kent, just a short drive from charming villages and historic landmarks. It has received very good ratings for cleanliness and user experience, and an excellent rating for its location.
The home features a spacious layout, perfect for accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a comfortable living room with a fireplace, a large deck with a grill and fire pit, and a private garden.
The House On High Meadow Farm - Kent, CT
10 14 reviews
Kent, CT
10/19 – 10/23
$646/nighttotal: $2584 (4 )

The House On High Meadow Farm

1 2
apartment , Sharon
This farmhouse is located in the scenic Housatonic River Valley, a short drive from Sharon, Connecticut, and close to the towns of Amenia and Wassaic in New York. The four-bedroom, two-bathroom farmhouse sleeps eight guests and features a swimming pool, air conditioning, and a peaceful country setting with stunning mountaintop views overlooking the Housatonic River Valley.
Sugarloaf Mountain Farm - Kent, CT
10 74 reviews
Kent, CT
10/19 – 10/23
$457/nighttotal: $1828 (4 )

Sugarloaf Mountain Farm

1 2
apartment , Kent
Sugarloaf Mountain Farm is located in the quiet hills of Litchfield County, Connecticut, just a short drive from the charming town of Kent. The farmhouse has consistently received excellent ratings for its cleanliness, location, and overall experience.
The entire house is available for guests, accommodating up to eight people comfortably. The farmhouse features a fully equipped kitchen, a screened porch, a large backyard with a fire pit, and a playset for children.

Best Kent, CT vacation rentals with parking

Litchfield County Getaway - Kent, CT
9.9 165 reviews
Kent, CT
08/01 – 08/03
$406/nighttotal: $812 (2 )

Litchfield County Getaway

3 2
apartment , Warren
This family-friendly vacation home is located in a peaceful rural setting near Warren, Connecticut, just 6 miles from Above All State Park, Lake Waramaug State Park, and the Housatonic River, perfect for nature lovers. The house consistently receives excellent ratings for location, cleanliness, and overall experience.
The 1860-square-foot house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a well-equipped kitchen, a spacious garden, a relaxing spa, and a private terrace, making it ideal for families and groups seeking a comfortable and enjoyable stay.
Creek Side Cabin With Wood Fired Hot Tub And Fire Pit - Kent, CT
9.5 2 reviews
Kent, CT
10/19 – 10/23
$480/nighttotal: $1920 (4 )

Creek Side Cabin With Wood Fired Hot Tub And Fire Pit

1 2
cabin , New Milford
The Creek Side Cabin in New Milford, Connecticut, is conveniently located within 23 miles of both the Russian Railway Museum and Flanders Nature Center.
This 700-square-foot one-bedroom cottage sleeps seven, boasting a fully equipped kitchen, jacuzzi, Wi-Fi, private parking, and outdoor space with a wood-fired hot tub and fire pit.
Hoppy Hill Farm House - Kent, CT
9.8 6 reviews
Kent, CT
08/01 – 08/03
$227/nighttotal: $454 (2 )

Hoppy Hill Farm House

1 2
apartment , Dover Plains
This one-bedroom apartment rental in Dover Plains, New York, is situated near the towns of Kent, Millbrook, Amenia, and Wassaic, providing easy access to the Appalachian Trail and attractions like the Harlem Valley Golf Club and Thunder Ridge Ski Resort.
The 1-bedroom unit, located in a 200-year-old farmhouse, features a queen bed, queen-size pull-out sofa, full kitchen, private entrance, and shared access to a large porch and 4-acre yard; it comfortably sleeps three guests and includes amenities such as Wi-Fi, air conditioning, and parking.
The Kent Collection - The Garden Cottages - Kent, CT
9.5 2 reviews
Kent, CT
10/19 – 10/23
$744/nighttotal: $2976 (4 )

The Kent Collection - The Garden Cottages

1 2
house , Kent
The Garden Cottages in Kent, Connecticut are located 24 miles from both the Flanders Nature Center and the Abbey of Regina Laudis, offering easy access to other attractions like Richter Park Golf Course and the Russian Railway Museum.
This 19th-century property provides pet-friendly accommodations with air conditioning, free Wi-Fi, private parking, and some units featuring fully equipped kitchens, a terrace, and a private garden with an outdoor fireplace.

Frequently Asked Questions about vacation rentals in Kent, CT

  • What sports or outdoor activites can visitors enjoy in and around Kent, CT?

    Kent is a great place for outdoor enthusiasts. You can go hiking, biking, fishing, and kayaking in the area. There are also several golf courses nearby. In the winter, cross-country skiing and snowshoeing are popular activities.
  • What are the best Airbnb and vacation rentals in Kent, CT?

    Loft 22, Spectacular Short Term Vacation Rental In Kent and Village Garden Townhouse are the most popular Airbnb and vacation rentals in Kent, CT among travelers.

  • What other towns or cities can be easily accessed from Kent, CT?

    Kent is conveniently located near several other towns and cities. You can easily drive to Litchfield, New Milford, and Danbury. If you're looking for a bigger city, Hartford is about an hour away.
  • What are the most popular Airbnbs in Kent, CT?

    Among the Airbnbs in Kent, CT, Loft 22, Village Garden Townhouse and Cheerful 2-bedroom House Porch And Fireplace are the most popular ones.

  • What amenities are commonly available in vacation rentals in Kent, CT?

    Vacation rentals in Kent usually come with amenities like kitchens, laundry facilities, and outdoor spaces like decks or patios. Many also offer fireplaces and hot tubs. You can find rentals with different levels of luxury, depending on your budget.
  • What are the best vacation rentals with a pool in Kent, CT?

  • What time of year is best to rent a vacation rental Kent, CT?

    The best time to visit Kent depends on your interests. Spring and fall offer mild weather and beautiful foliage. Summer is great for outdoor activities, and winter is ideal for enjoying the snow.
  • What are the best rentals for families and kids in Kent, CT?

  • What are the local dishes in Kent, CT region?

    The local cuisine in Kent is a mix of New England classics and modern American fare. You'll find plenty of seafood restaurants, as well as farm-to-table options. Be sure to try some of the local apple cider donuts - they're a must-try!
  • What are the best rentals or Airbnbs with a jacuzzi in Kent, CT?

    The best vacation rental or Airbnb with a jacuzzi in Kent, CT is Beautiful Barn W/ Pond Views- Pool & Hot Tub Open.

Destinations nearby

Guest-Favorite Vacation Rentals with a Terrace in Kent, CT

Elevate your stay in Kent, CT with a vacation rental featuring a private balcony and stunning city skyline views.

Gunn Brook Mountain House - Kent, CT
Kent, CT
10/19 – 10/23
$309/nighttotal: $1236 (4 )

Gunn Brook Mountain House

1 2
house , Cornwall
Gunn Brook Mountain House, a beachfront home in Cornwall, Connecticut, is 22 miles from both the Abbey of Regina Laudis and Flanders Nature Center, and 47 miles from Bradley International Airport.
This 2,000-square-foot vacation rental sleeps up to 11 guests and boasts a private beach, fitness center, three bathrooms, and amenities including Wi-Fi, a fireplace, and a dartboard.
Creek Side Cabin With Wood Fired Hot Tub And Fire Pit - Kent, CT
10 3 reviews
Kent, CT
10/19 – 10/23
$600/nighttotal: $2400 (4 )

Creek Side Cabin With Wood Fired Hot Tub And Fire Pit

1 2
cabin , New Milford
This Sherman, Connecticut waterfront cottage, minutes from New Milford and near Candlewood Lake and Squantz Pond State Park, offers easy access to hiking trails and the Elephant's Trunk Flea Market.
The 700-square-foot, two-bedroom, one-bathroom rental sleeps four, features a wood-fired hot tub, creekside outdoor shower (seasonal), kayaks, and a fully equipped kitchen with a s'mores kit.

Neighborhoods and points of interest in Kent, CT

Top-Rated Pet-Friendly Vacation Rentals in Kent, CT

Travel with ease to Kent, CT with pet-friendly rentals located near local dog parks and scenic city walks.

Artist Room At The Wandering Peacock - Kent, CT
9.8 398 reviews
Kent, CT
10/19 – 10/23
$421/nighttotal: $1684 (4 )

Artist Room At The Wandering Peacock

1 2
studio , Kent
The Wandering Peacock is a charming studio nestled in the foothills of the Appalachian Trail, within walking distance of Bulls Bridge and just minutes from downtown Kent. The studio has excellent user, location, and cleanliness ratings.
The studio features an eclectic artistic style with original paintings, stained glass, and hand-painted silk linens. It has a full kitchen, dining room, and dance studio with full mirrors for guests' use. The studio also has private gardens, a fire pit area, and resident peacocks and chickens. It has air conditioning, a Jacuzzi, a garden, and parking.
Escape To A One-of-a-kind Mountaintop Retreat With Panoramic Westerly Views - Kent, CT
Kent, CT
10/19 – 10/23
$535/nighttotal: $2140 (4 )

Escape To A One-of-a-kind Mountaintop Retreat With Panoramic Westerly Views

3 2
apartment , New Milford
This New Milford vacation rental, located 75 miles from NYC near Lake Waramaug State Park and several golf courses including Bull’s Bridge Golf Course, offers stunning scenic views and easy access to area attractions.
The three-bedroom, three-bathroom home features an open-plan main floor with a stone fireplace, a finished basement game room with ping pong, darts, foosball, and shuffleboard, and a private deck or enclosed porch with a firepit; it comfortably sleeps six guests and includes central air conditioning and internet access.
Modern Mountaintop Log Cabin & Sauna - Kent, CT
9.9 64 reviews
Kent, CT
10/19 – 10/23
$588/nighttotal: $2352 (4 )

Modern Mountaintop Log Cabin & Sauna

4 2
cabin , Kent
This secluded mountaintop cabin in Kent offers stunning views, just minutes from Kent's amenities and attractions. It has received excellent ratings for its location, cleanliness, and overall experience.
The cabin features four bedrooms, three bathrooms, and can accommodate up to eight guests. It has a spacious great room with cathedral ceilings and a fireplace, a wrap-around porch, a lofted balcony, and a finished lower level with a recreation room, full bath, laundry, and garage. The cabin is also pet-friendly and has a small dog on the premises.
Kent Village Home 2 Hrs From Nyc - Kent, CT
9.8 147 reviews
Kent, CT
08/01 – 08/03
$856/nighttotal: $1712 (2 )

Kent Village Home 2 Hrs From Nyc

4 2
apartment , Kent
This completely renovated Dutch Colonial house in Kent, Connecticut, is centrally located within walking distance of Main Street's restaurants, shops, and the Appalachian Trail, and a short drive from Mohawk Mountain Ski Area and Kent Falls.
This four-bedroom, two-and-a-half-bathroom home sleeps seven guests and features a private courtyard deck, in-unit amenities including a dishwasher and air conditioning, and access to the entire house (excluding the attic) plus parking.
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