Holiday Rentals in Kent, CT

36 available vacation rental offers

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Kent, CT holiday rentals
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Best Holiday rentals and Airbnb offers in Kent, CT

Best family friendly Kent, CT holiday rentals

Among the 36 accommodations in Kent, CT, here are the 4 best family friendly rentals

Tranquil Country Escape With New Pool/hot Tub - Kent, CT
9.5 82 reviews
Kent, CT
19/10 – 23/10
SG$641/nighttotal: SG$2564 (4 )

Tranquil Country Escape With New Pool/hot Tub

1 2
apartment , Warren
This apartment is located in a tranquil setting in Warren, Connecticut, just 6 kilometres from Kent and Lake Waramaug, and 16 kilometres from Bantam. The property has consistently received excellent guest reviews for its cleanliness, location, and overall experience.
The self-catering home sleeps up to 6 guests in its 3 bedrooms and 2 bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden with a swimming pool and hot tub, plus entertainment options such as a ping pong table, dart board, and pop-a-shot.
Historic Warren/kent Home - Kent, CT
9.7 107 reviews
Kent, CT
19/10 – 23/10
SG$505/nighttotal: SG$2020 (4 )

Historic Warren/kent Home

3 2
apartment , Warren
This historic home is located on the border of Warren and Kent, Connecticut, just 1.6 km from both town centres and Mohawk Mountain ski resort, offering a peaceful rural setting. The property has received excellent ratings for its location, cleanliness, and overall experience.
The spacious apartment has three bedrooms and three bathrooms, covering 260 square metres. It boasts a fully equipped kitchen, a terrace, a garden, and parking, as well as a walking path on the five-acre property, perfect for exploring the surrounding nature.
Hoppy Hill Farm House - Kent, CT
9.4 7 reviews
Kent, CT
01/08 – 02/08
SG$347/nightfor 1 night

Hoppy Hill Farm House

1 2
house , Dover Plains
Hoppy Hill Farm House, a one-bedroom property in Dover Plains, New York, is situated approximately 34-38km from attractions including Richter Park Golf Course, Vassar College, the Mid-Hudson Children's Museum, and the Bardavon Opera House.
This self-catering cottage offers 46 square metres of space, sleeping up to five guests and boasting a fully equipped kitchen, garden, parking, air conditioning, and free Wi-Fi.
The House On High Meadow Farm - Kent, CT
10 14 reviews
Kent, CT
19/10 – 23/10
SG$831/nighttotal: SG$3324 (4 )

The House On High Meadow Farm

1 2
apartment , Sharon
This farmhouse is situated in the Housatonic River Valley, approximately 10 kilometres from Kent, Connecticut, providing easy access to Sharon's attractions.
The property boasts four bedrooms, two bathrooms, and a swimming pool, making it ideal for families or groups of up to eight guests seeking a peaceful retreat.

Best Kent, CT holiday rentals with parking

Artistic Barn: Wood Burning Hottub, Sauna And Pizza Oven - Kent, CT
9.4 6 reviews
Kent, CT
19/10 – 23/10
SG$696/nighttotal: SG$2784 (4 )

Artistic Barn: Wood Burning Hottub, Sauna And Pizza Oven

3 2
apartment , Kent
This five-bedroom riverside property in Kent, Connecticut, is situated less than 1.6km from the Housatonic River and Bull's Bridge, and 4.3km from the Herrick Preserve, offering easy access to outdoor activities.
Sleeping up to eleven guests, this self-catering holiday home boasts three bathrooms, a fully equipped kitchen including dishwasher, a jacuzzi, sauna, free Wi-Fi, and BBQ facilities, ensuring a comfortable and relaxing stay.
Hillside Grove - Kent, CT
9.9 81 reviews
Kent, CT
01/08 – 02/08
SG$1215/nightfor 1 night

Hillside Grove

1 2
apartment , Dover Plains
This Dover Plains country house retreat boasts expansive views and is conveniently located for exploring local attractions.
The four-bedroom, two-bathroom property sleeps eight guests and features a fully equipped kitchen, jacuzzi, expansive patio with Blackstone grill and hot tub, a family game room, and 1 Gig internet access.
Unique Geodesic Dome Escape In Nature! - Kent, CT
10 1 review
Kent, CT
19/10 – 23/10
SG$605/nighttotal: SG$2420 (4 )

Unique Geodesic Dome Escape In Nature!

3 2
apartment , Warren
This Cornwall Bridge lodge, located in Litchfield County, Connecticut, is near Candlewood Lake and Kent Falls State Park.
The 212-square-metre (2280 sq ft) property sleeps six, boasting three bedrooms, two bathrooms, a fully equipped kitchen (including a dishwasher in each bedroom), a private patio with BBQ facilities, and in-unit laundry.
Creek Side Cabin With Wood Fired Hot Tub And Fire Pit - Kent, CT
9.5 2 reviews
Kent, CT
19/10 – 23/10
SG$617/nighttotal: SG$2468 (4 )

Creek Side Cabin With Wood Fired Hot Tub And Fire Pit

1 2
cabin , New Milford
The Creek Side Cabin is situated in New Milford, Connecticut, approximately 37 kilometres from both the Russian Railway Museum and the Flanders Nature Center.
This self-catering lodge boasts a 65-square-metre floor area, featuring one bedroom, one bathroom, and a Jacuzzi, comfortably accommodating up to seven guests; enjoy its wood-fired hot tub, fire pit and private garden.

Frequently asked questions about holiday rentals in Kent, CT

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

    Kent is a haven for outdoor enthusiasts. You can go hiking, mountain biking, kayaking, or fishing in the nearby lakes and rivers. The area is also popular for cross-country skiing and snowshoeing in the winter.
  • 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 ideally situated for exploring the surrounding area. You can easily reach Litchfield, New Milford, and Danbury by car. For a bigger city experience, head to Waterbury or Hartford, which are both around a 45-minute drive 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 often come with amenities such as a kitchen, laundry facilities, and Wi-Fi. Many also have fireplaces, outdoor decks, and hot tubs. You can find a variety of properties, from cozy cottages to spacious houses.
  • 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 preferences. Summer offers warm weather for outdoor activities, while autumn brings beautiful foliage and cooler temperatures. Spring and winter are quieter and offer a different charm.
  • What are the best rentals for families and kids in Kent, CT?

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

    The region is known for its fresh, locally sourced ingredients. You can find delicious New England clam chowder, lobster rolls, and other seafood dishes. There are also many farm-to-table restaurants serving up seasonal menus with local produce.
  • What are the best rentals or Airbnbs with a jacuzzi in Kent, CT?

    Beautiful Barn W/ Pond Views- Pool & Hot Tub Open and Artistic Concered Barn are the best vacation rentals or Airbnb with a jacuzzi in Kent, CT.

Destinations nearby

Best Kent, CT holiday rentals with a balcony

Gunn Brook Mountain House - Kent, CT
Kent, CT
19/10 – 23/10
SG$397/nighttotal: SG$1588 (4 )

Gunn Brook Mountain House

1 2
house , Cornwall
Gunn Brook Mountain House, a beachfront property in Cornwall, is situated 35km from both the Abbey of Regina Laudis and Flanders Nature Centre, and 76km from Bradley International Airport.
This 186 square metre house sleeps 11, boasting three bathrooms, a fully equipped kitchen, fitness centre, private beach access, and a terrace with mountain views; nearby hiking trails and a dartboard provide additional entertainment.
Fabulous Year Round Waterfront Retreat On Lake Waramaug - Kent, CT
10 7 reviews
Kent, CT
01/08 – 03/08
SG$2437/nighttotal: SG$4874 (2 )

Fabulous Year Round Waterfront Retreat On Lake Waramaug

3 2
apartment , Washington
This apartment is located in New Preston, Connecticut, a charming village just 100km from Washington, offering a peaceful escape from the city bustle. The property has received excellent guest reviews and is a perfect choice for those seeking a relaxing getaway.
The apartment offers 211 square meters of space, with three bedrooms, three bathrooms, and a capacity for eight guests. Enjoy a range of amenities, including a fully equipped kitchen, a jacuzzi, a terrace, a garden, and a spa, as well as access to nearby hiking trails, vineyards, and local attractions.
Hoppy Hill Farm House - Kent, CT
9.8 6 reviews
Kent, CT
01/08 – 02/08
SG$359/nightfor 1 night

Hoppy Hill Farm House

1 2
apartment , Dover Plains
This Dover Plains condo, a short drive (approximately 26km) from Candlewood Lake and 13km from the Housatonic River, offers convenient access to Harlem Valley Golf Club and Thunder Ridge Ski Resort.
This self-catering apartment sleeps three guests, featuring a fully equipped kitchen with microwave and fridge, a private balcony and garden, plus on-site parking and BBQ facilities.
Creek Side Cabin With Wood Fired Hot Tub And Fire Pit - Kent, CT
10 3 reviews
Kent, CT
19/10 – 23/10
SG$772/nighttotal: SG$3088 (4 )

Creek Side Cabin With Wood Fired Hot Tub And Fire Pit

1 2
cabin , New Milford
This Sherman, Connecticut lodge is situated a short drive (approximately 10km) from New Milford and offers easy access to Candlewood Lake and Squantz Pond.
The 65-square-metre property sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen, a wood-fired hot tub, and kayaks for guest use, alongside access to nearby hiking trails and the Elephant's Trunk Flea Market.

Best pet friendly Kent, CT holiday rentals

Among the 36 accommodations in Kent, CT, here are the 4 best pet friendly rentals

The Perfect Getaway Cabin - Kent, CT
9.8 31 reviews
Kent, CT
01/08 – 03/08
SG$623/nighttotal: SG$1246 (2 )

The Perfect Getaway Cabin

3 2
cabin , Washington
This Washington cabin is situated on 20 acres of land, just a short distance from hiking trails and a tranquil pond. It has received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The comfortable retreat has three bedrooms and one bathroom, accommodating up to six guests. The cabin offers a fully equipped kitchen, a wrap-around deck with outdoor seating, a fire pit, a barbecue, and access to streaming services, board games, and books.
Peaceful Cabin With Sauna, Hot Tub & Cold Plunge - Kent, CT
10 6 reviews
Kent, CT
01/08 – 03/08
SG$819/nighttotal: SG$1638 (2 )

Peaceful Cabin With Sauna, Hot Tub & Cold Plunge

2 2
cabin , Cornwall
The Little Bell Cabin, a self-catering cottage near Cornwall, Connecticut, offers easy access to local wineries and breweries, as well as attractions such as Music Mountain and the Connecticut Antique Machinery Association.
This 60 square metre (646 square feet) retreat sleeps four in two bedrooms and one bathroom, boasting a fully equipped kitchen, a hot tub, a wood-fired fire pit, and a spacious deck; nearby activities include e-bike rentals and access to hiking trails.
Country Retreat With Pool 10 Mn From Kent Ct - Kent, CT
10 6 reviews
Kent, CT
19/10 – 23/10
SG$804/nighttotal: SG$3216 (4 )

Country Retreat With Pool 10 Mn From Kent Ct

3 2
apartment , Kent
This Kent, Connecticut mountainside property is situated approximately 3km from Lake Waramaug State Park and within 10km of Hopkins Vineyard and Mount Bushnell State Park, offering easy access to outdoor activities.
This three-bedroom, two-bathroom house sleeps seven guests and boasts a private outdoor pool, patio, fully equipped kitchen, free Wi-Fi, and a fireplace; nearby attractions include opportunities for swimming, boating, fishing, wine tasting, and hiking.
Kent Village Home 2 Hrs From Nyc - Kent, CT
9.8 147 reviews
Kent, CT
01/08 – 03/08
SG$1100/nighttotal: SG$2200 (2 )

Kent Village Home 2 Hrs From Nyc

4 2
apartment , Kent
This recently renovated Dutch colonial residence in Kent, Connecticut, offers a prime location within 500 meters of Main Street's shops, restaurants, and art galleries, and is also conveniently close to Kent School.
This 4-bedroom property accommodates up to 7 guests, featuring 2.5 bathrooms, air conditioning, a dishwasher, and a private courtyard deck, with easy access to outdoor pursuits such as Mohawk Mountain Ski Area and Kent Falls, and a 15-minute drive to the Harlem Valley-Wingdale Metro-North station.
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