Best Holiday rentals and Airbnb offers in Kent, CT
10 7 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.
10 14 reviews
Kent, CT
19/10 – 23/10
SG$836/nighttotal: SG$3344 (4 )
Kent Collection | Garden Cottages | The Train Car
1 2
apartment , Kent
The Train Car B&B is situated in Kent, Connecticut, a short walk from the town centre and a scenic 10-kilometre drive from Kent Falls State Park. The property has received excellent ratings for location, cleanliness, and overall guest experience. The charming B&B is housed in a renovated 1800s baggage car, offering a unique and comfortable stay for up to four guests. The Train Car B&B provides a fully equipped kitchen, a private garden, and air conditioning for a relaxing and enjoyable stay.
9.9 65 reviews
Kent, CT
01/08 – 03/08
SG$347/nighttotal: SG$694 (2 )
Charming Home In Kent
2 2
apartment , Kent
This Kent, Connecticut home, situated on a tree-filled knoll approximately 24km from Mohawk Mountain ski area and Lake Waramaug, offers easy access to Litchfield County's attractions. The two-bedroom property sleeps four, boasting a recently renovated kitchen with modern appliances, a living room with a piano, a separate TV room, and a garden; solar energy powers the house, and high-speed internet is available.
10 13 reviews
Kent, CT
19/10 – 23/10
SG$426/nighttotal: SG$1704 (4 )
Cozy Hillside Retreat Close To Kent
1 2
apartment , Kent
The Nest guesthouse is situated in the Litchfield Hills, just a few kilometres from the restaurants, shops, and galleries of Kent town centre. The surrounding area offers a peaceful and tranquil setting, perfect for a relaxing getaway. The guesthouse has two bedrooms and one bathroom, comfortably accommodating up to four guests. The modern, open-plan living area features a gas fireplace, a well-equipped kitchen, and a private outdoor deck with stunning views, while the shared lap pool is available during the summer months.
9.8 31 reviews
Kent, CT
19/10 – 23/10
SG$569/nighttotal: SG$2276 (4 )
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.
9.8 58 reviews
Kent, CT
01/08 – 03/08
SG$626/nighttotal: SG$1252 (2 )
Beautiful Barn W/ Pond Views. Pool/hot Tub/sauna
3 2
apartment , Kent
This secluded 25-acre former summer camp, located just under 10 minutes from Kent and approximately 32 kilometers from the Harlem-Valley Wingdale train station, offers a private countryside escape 132 kilometers north of NYC. This exceptional 3-bedroom, 2-bathroom silo-barn house, accommodating up to 4 guests, features a gourmet kitchen with a stove and fireplace, a new sauna in a gazebo, a private pond for fishing and canoeing, and is equipped with air conditioning, Wi-Fi, a swimming pool, and Jacuzzi.
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.
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.
9.2 10 reviews
Kent, CT
19/10 – 23/10
SG$910/nighttotal: SG$3640 (4 )
Kent’s Best Waterfront In-town! (3 Queen Beds)
1 2
apartment , Kent
This Kent riverfront cottage, a two-minute walk from Kent town centre and 1.3km from Kent School, offers secluded panoramic views. Sleeping up to six guests across three bedrooms (two queen beds and a loft suite) and one bathroom, this property boasts a petite gourmet kitchen, 74 square metre wraparound deck, Yamaha baby grand piano, screened sleeping porch, and beautiful gardens attracting hummingbirds and bald eagles.
10 5 reviews
Kent, CT
19/10 – 23/10
SG$520/nighttotal: SG$2080 (4 )
Unique Geodesic Dome Escape In Nature!
3 2
apartment , Warren
This Warren, Litchfield Hills, Connecticut lodge is situated on a secluded 2.5-acre property near scenic trails and wineries, offering easy access to Kent Falls State Park. The three-bedroom, two-bathroom retreat sleeps six, boasts a fully equipped kitchen with modern appliances, a dedicated workspace, outdoor amenities including a deck, gas fire pit and electric BBQ, and access to an organic vegetable garden.
9.6 139 reviews
Kent, CT
19/10 – 23/10
SG$297/nighttotal: SG$1188 (4 )
Country Guest Cottage/barn
1 2
farm , Kent
This charming farm stay is located in Litchfield County, just 3 kilometres from Lake Waramaug and a short drive from several picturesque towns, including Kent, Bantam and Litchfield. The property has received excellent ratings for its cleanliness, location and overall experience, making it a popular choice for travellers seeking a peaceful escape. The cottage offers a unique blend of rustic charm and modern comfort, sleeping up to four guests. Guests have access to a fully equipped kitchen, a private garden, and plenty of parking, along with nearby hiking trails, ponds, and lakes for outdoor exploration.
9.1 25 reviews
Kent, CT
01/08 – 02/08
SG$573/nightfor 1 night
Sharon Country Estate On 300 Acres
3 2
apartment , Sharon
This apartment is located on a 300-acre estate in Sharon, Connecticut, close to a 2000-acre natural wildlife sanctuary and a short drive from Connecticut State Highway 4. It boasts excellent user, location and cleanliness ratings. The self-catering property has four bedrooms and three bathrooms, accommodating up to six guests. It includes a kitchen, parking, internet access, two fireplaces, and stunning views of the surrounding hills.
Best family friendly Kent, CT holiday rentals
Among the 36 accommodations in Kent, CT, here are the 4 best family friendly rentals
9.5 2 reviews
Kent, CT
19/10 – 23/10
SG$957/nighttotal: SG$3828 (4 )
The Kent Collection - The Garden Cottages
1 2
house , Kent
The Garden Cottages are situated in Kent, approximately 39 kilometres from both the Flanders Nature Centre and the Abbey of Regina Laudis. This 19th-century property offers self-catering accommodation with free Wi-Fi, private parking, air conditioning, and a terrace; guests can enjoy the on-site garden, outdoor fireplace, and proximity to local attractions.
10 15 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.
10 216 reviews
Kent, CT
01/08 – 03/08
SG$433/nighttotal: SG$866 (2 )
Private New House On 10 Acres Of Pristine Nature
3 2
apartment , Warren
This charming house is located just outside Warren, within easy reach of hiking trails, a pond, and a selection of restaurants, galleries and shops. The accommodation has consistently received excellent ratings for its location, cleanliness and overall experience. The house is spread over three floors and can accommodate up to six guests. It features a fully equipped kitchen, a spacious living area, a dedicated TV room, a private garden, a fitness centre and parking.
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.
Best Kent, CT holiday rentals with parking
9.9 85 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.
10 3 reviews
Kent, CT
19/10 – 23/10
SG$596/nighttotal: SG$2384 (4 )
Unique Geodesic Dome Escape In Nature!
3 2
house , Warren
This Warren house, sleeping up to 11 guests, is situated in a location not specified in the provided details. The 212 square metre property boasts three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, a garden, parking, and free Wi-Fi.
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.
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.
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?
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 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?
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?
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.
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.
9.8 9 reviews
Kent, CT
01/08 – 03/08
SG$524/nighttotal: SG$1048 (2 )
Quiet Historic Retreat
4 2
apartment , New Milford
This Gaylordsville flat is located near New Milford and Kent, offering convenient access to antique shops, restaurants, and outdoor pursuits along the Housatonic River, with the Old Oak Tavern just a short walk away. This four-bedroom, two-bathroom apartment accommodates six guests and features a well-equipped kitchen with a dishwasher and microwave, air conditioning, a balcony, and a large soaking tub, with nearby fishing, hiking, and ski resorts like Mohawk and Thunder Ridge within approximately 48 kilometres.
9.8 6 reviews
Kent, CT
01/08 – 03/08
SG$292/nighttotal: SG$584 (2 )
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.
Best pet friendly Kent, CT holiday rentals
Among the 36 accommodations in Kent, CT, here are the 4 best pet friendly rentals
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.
9.9 64 reviews
Kent, CT
19/10 – 23/10
SG$756/nighttotal: SG$3024 (4 )
Modern Mountaintop Log Cabin & Sauna
4 2
cabin , Kent
This charming cabin is located near Kent, a short distance from Sharon, Wassaic, Mohawk Ski Area, the Appalachian Trail, local restaurants, and art galleries. The surrounding area offers a peaceful retreat amidst stunning natural beauty, making it ideal for those seeking a tranquil escape. The cabin has consistently received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers. The property features four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The cabin offers a range of modern amenities including a fully equipped kitchen, air conditioning, a fireplace, a spacious living area, a recreation room, and a wrap-around porch and deck with stunning views of the surrounding landscape.
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.
9.9 212 reviews
Kent, CT
19/10 – 23/10
SG$376/nighttotal: SG$1504 (4 )
Vibrant, Secluded Dome Home In Litchfield County!
3 2
cabin , Cornwall
This bubble is located in Litchfield County, Connecticut, just 10 kilometres from Mohawk Mountain Ski Area and Lake Waramaug, offering a peaceful retreat in a scenic setting. It has received excellent ratings for user experience, location, and cleanliness. This unique dome-shaped dwelling can accommodate up to 8 guests, and features a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, a garden, and parking. Guests can enjoy a variety of activities on-site and nearby, including hiking, kayaking, fishing, skiing, and exploring the Connecticut Wine Trail.