Search vacation rentals in Kent, CT from 100+ sites!

36 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Kent, CT vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

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.
Cozy Country Cabin - Kent, CT
10 5 reviews
Kent, CT
08/01 – 08/03
$197/nighttotal: $394 (2 )

Cozy Country Cabin

1 2
apartment , Cornwall
This 1-bedroom, 1-bathroom apartment in Cornwall offers internet, a kitchen, and parking for up to 2 guests, located in the Housatonic River Valley a short drive from Kent Falls and 15 miles from the 10 Mile train station. Enjoy outdoor activities like hiking and fishing, relax in the jacuzzi tub or with the massage chair, and utilize the deck with BBQ facilities, with fine dining options nearby.
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.

Best Kent, CT vacation rentals with parking

Peaceful Cabin With Sauna, Hot Tub & Cold Plunge - Kent, CT
10 6 reviews
Kent, CT
08/01 – 08/03
$637/nighttotal: $1274 (2 )

Peaceful Cabin With Sauna, Hot Tub & Cold Plunge

2 2
cabin , Cornwall
The Little Bell Cabin, a Cornwall, Connecticut getaway, sits in the Berkshire Mountains foothills near Mohawk Mountain and Hopkins Winery, offering easy access to outdoor recreation.
This 650-square-foot cottage features two queen bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, propane fireplace, hot tub, and Weber grill for a relaxing retreat.
Fabulous Year Round Waterfront Retreat On Lake Waramaug - Kent, CT
10 7 reviews
Kent, CT
08/01 – 08/03
$1896/nighttotal: $3792 (2 )

Fabulous Year Round Waterfront Retreat On Lake Waramaug

3 2
apartment , Washington
This charming vacation rental is located in New Preston, a short walk from the Pinnacle Trail and a half-mile from the village center, offering a peaceful and scenic retreat near Lake Waramaug. The apartment has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and relaxing stay.
The 2270-square-foot apartment has three bedrooms, three bathrooms, and can accommodate up to eight guests. The apartment features a fully equipped kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a Jacuzzi, a terrace, a garden, a spa, and parking.
Hillside Grove - Kent, CT
9.9 81 reviews
Kent, CT
08/01 – 08/02
$945/nightfor 1 night

Hillside Grove

1 2
apartment , Dover Plains
This Dover Plains country house rental boasts four bedrooms, two bathrooms, and sleeps eight, offering easy access to local hiking trails and wineries; precise distances to specific landmarks require further inquiry.
The 4-bedroom house features a fully equipped kitchen, expansive patio with a Blackstone grill and hot tub, a cozy deck with a fire pit, a sunroom, a lower level game room with a queen bed, and 1 gigabit internet access; lawn games and a variety of indoor games and books are also available for guest enjoyment.

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.

Fabulous Year Round Waterfront Retreat On Lake Waramaug - Kent, CT
10 7 reviews
Kent, CT
08/01 – 08/03
$1896/nighttotal: $3792 (2 )

Fabulous Year Round Waterfront Retreat On Lake Waramaug

3 2
apartment , Washington
This charming vacation rental is located in New Preston, a short walk from the Pinnacle Trail and a half-mile from the village center, offering a peaceful and scenic retreat near Lake Waramaug. The apartment has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and relaxing stay.
The 2270-square-foot apartment has three bedrooms, three bathrooms, and can accommodate up to eight guests. The apartment features a fully equipped kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a Jacuzzi, a terrace, a garden, a spa, and parking.
Hoppy Hill Farm House - Kent, CT
9.8 6 reviews
Kent, CT
08/01 – 08/02
$279/nightfor 1 night

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.
Quiet Historic Retreat - Kent, CT
9.8 9 reviews
Kent, CT
08/01 – 08/03
$408/nighttotal: $816 (2 )

Quiet Historic Retreat

4 2
apartment , New Milford
This 4-bedroom, 2-bathroom apartment in Gaylordsville, near New Milford, offers a quiet hillside setting with audible Housatonic River sounds, located 30 miles from Mohawk Mountain and Thunder Ridge Ski Mountains, and within walking distance of restaurants like the Old Oak Tavern.
This accommodation features a large kitchen with an island, a dining table for six, a soaking tub, and four sleeping spaces, including two queen bedrooms and a daybed in a converted office, with internet and air conditioning provided for up to six guests.

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.

Appalachian Getaway - Kent, CT
10 17 reviews
Kent, CT
08/01 – 08/02
$411/nightfor 1 night

Appalachian Getaway

2 2
apartment , Sherman
This barn apartment is located in the hills of Western Connecticut, near Sherman, with easy access to the Appalachian Loop and River Oaks Golf Club. The surrounding area offers a peaceful escape from city life and is close to scenic hiking trails and natural beauty.
This two-bedroom loft can accommodate up to four guests. The apartment comes with a kitchen, air conditioning, parking, internet, and access to a private beach.
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.
©2026 cozycozy.com