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

Top-Rated Vacation Rentals near the City Center in Kent, CT

Stay in downtown Kent, CT to keep top attractions within walking distance. Browse our central vacation rentals and find your perfect base.

Kent Collection | Garden Cottages | The Bunk House - Kent, CT
10 4 reviews

Kent Collection | Garden Cottages | The Bunk House

cottage, Kent
This charming cottage is located just a short drive from Canterbury, offering easy access to the city's historic attractions, while still providing a peaceful retreat in the Kent countryside. Guests consistently rate the cottage excellent for its location, cleanliness, and overall experience.
The cottage has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, air conditioning, a garden, parking, and internet access, making it perfect for a relaxing and enjoyable stay.
Kents Best Waterfront In-town! (3 Queen Beds) - Kent, CT
9.4 14 reviews

Kents Best Waterfront In-town! (3 Queen Beds)

apartment, Kent
This Kent, Washington riverfront cottage is a two-minute walk from downtown Kent and less than a mile from Kent School, offering secluded panoramic views.
The 1400-square-foot home features three queen beds sleeping five to six guests, a petite gourmet kitchen, a Yamaha baby grand piano, a large 800-square-foot wraparound deck, and screened sleeping porch overlooking courtly gardens.
Kent Collection | Garden Cottages | The Train Car - Kent, CT
10 14 reviews

Kent Collection | Garden Cottages | The Train Car

cottage, Kent
This Kent, Washington studio, located in the Station area, is a two-minute walk from shops and restaurants, across from the Kent Library, and next to a restaurant with live music.
This unique unit, a repurposed 1800s baggage car, features a queen bed, two twin daybeds, a kitchenette with a fridge, microwave, and burners, a private patio with Adirondack chairs and a firepit, and accommodates up to four guests.
Kent Village Apartment - Kent, CT
10 6 reviews

Kent Village Apartment

apartment, Kent
This newly renovated second-floor apartment in Kent, Connecticut, is located within walking distance of local dining and retail, and a short drive from Kent School, the Appalachian Trail, and Kent Falls State Park.
This two-bedroom flat accommodates up to four guests and features a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and internet.

Best Kent, CT vacation rentals with air conditioning

The Wheelhaus Restored Home In Hamlet Of Amenia - Kent, CT
10 9 reviews

The Wheelhaus Restored Home In Hamlet Of Amenia

apartment, Amenia
This vacation home is located in Amenia, a peaceful rural area, just minutes from the Metro North train station and close to the town center with restaurants, cafes, and a drive-in movie theater. The property has received excellent user ratings, making it a popular choice for travelers seeking a relaxing getaway.
This 3-bedroom, 2-bathroom house spans 1250 square feet and comfortably accommodates up to 6 guests. Enjoy modern farmhouse style with amenities like air conditioning, a fully equipped kitchen, a garden, parking, and internet access.
Deck & Wooded Views! 2 Mi To Frederick Gunn School - Kent, CT
No reviews

Deck & Wooded Views! 2 Mi To Frederick Gunn School

apartment, Washington
This Washington, D.C. condo offers a prime location with easy access to the National Mall, White House, and Capitol Building, situated within 1 mile of major tourist attractions and government buildings.
This one-bedroom, one-bathroom rental spans 1100 square feet and accommodates up to five guests, featuring a full kitchen with a fridge and microwave, air conditioning, spa access, and parking, with public transportation readily available for exploring the city.
Lake Waramug Cottage Washington Ct- Ski Mohawk - Kent, CT
9.7 59 reviews

Lake Waramug Cottage Washington Ct- Ski Mohawk

apartment, Washington
This charming cottage sits on the shores of Lake Waramaug in the Litchfield Hills, a short drive from New Preston shops and Avril Farm. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy modern amenities, including a recently updated kitchen and bathroom, fast Wi-Fi, and access to a shared lakefront deck, kayaks, and a pavilion.
New! Secluded Guesthouse For Serene Getaway - Kent, CT
10 1 review

New! Secluded Guesthouse For Serene Getaway

house, Washington
This private guest home is located on a large estate in Litchfield County, a short drive from New Preston and Washington Depot, and close to Lake Waramaug and Steep Rock Preserve.
This accommodation offers a queen-size bedroom, a full kitchen, a living room, and parking, with extensive outdoor space including decks and a screened-in patio, and is suitable for up to 3 guests.

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.

Popular destinations

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.

Escape To Your Private Lakeside Estate! Family & Dog Friendly, Wildlife Viewing! - Kent, CT
10 131 reviews

Escape To Your Private Lakeside Estate! Family & Dog Friendly, Wildlife Viewing!

apartment, Dover Plains
This Dover Plains vacation home is located in Wingdale, a short drive from the Housatonic River and Bull's Bridge, offering easy access to outdoor activities and scenic beauty. Guests rave about the excellent user ratings, highlighting the comfortable and well-equipped accommodation.
This spacious 4-bedroom, 3-bathroom house comfortably accommodates up to 11 guests, providing plenty of room for families or groups. Enjoy features like a private fitness center, a tennis court, and a Jacuzzi, along with a fully equipped kitchen, a terrace, and a garden, all perfect for relaxing and enjoying your stay.
Creek Side Cabin With Wood Fired Hot Tub And Fire Pit - Kent, CT
9.3 3 reviews

Creek Side Cabin With Wood Fired Hot Tub And Fire Pit

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.
Creek Side Cabin With Wood Fired Hot Tub And Fire Pit - Kent, CT
10 3 reviews

Creek Side Cabin With Wood Fired Hot Tub And Fire Pit

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.
Hoppy Hill Farm House - Kent, CT
9.8 6 reviews

Hoppy Hill Farm House

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.

Neighborhoods and points of interest 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
10 228 reviews

Private New House On 10 Acres Of Pristine Nature

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.
Lakeside Country Home In Northwestern Connecticut - Kent, CT
No reviews

Lakeside Country Home In Northwestern Connecticut

apartment, Kent
This 4-bedroom cottage is located in Kent, Connecticut, a short drive from the town center, Mohawk Mountain, and Lake Waramaug State Park. The cottage features a private lake with kayaking and paddleboarding, a movie room, a barrel sauna and hot tub, and a large porch with lake views.
Kent Midcentury Modern - Kent, CT
8.0 5 reviews

Kent Midcentury Modern

bungalow, Kent
This midcentury ranch-style bungalow in Kent, Connecticut, is located a short walk from the Appalachian Trail and Housatonic River, and less than 1 mile from Kent village center.
This family-friendly property accommodates 8 guests with 3 bedrooms and 2 bathrooms, featuring a sunroom with a dining table for 8, a patio with a charcoal grill and fire pit, and air conditioning.
Two Bedroom Cottage Close To Town - Kent, CT
9.4 32 reviews

Two Bedroom Cottage Close To Town

cottage, Sharon
This charming cottage is located in Sharon, just 90 minutes from the city and minutes from the town center, offering a peaceful retreat in a picturesque setting. It has consistently received excellent ratings from previous guests.
The cottage features two bedrooms and two bathrooms, accommodating up to six guests comfortably. Amenities include a fully equipped kitchen, a cozy living room with a fireplace, a private backyard, and a Jacuzzi.

Best Kent, CT vacation rentals with parking

Zen Peaceful, Light Filled - Kent, CT
9.0 4 reviews

Zen Peaceful, Light Filled

apartment, Washington
Washington,  Ct Barn Hideaway. - Kent, CT
10 19 reviews

Washington, Ct Barn Hideaway.

apartment, Washington
Magical Woodland Getaway - Kent, CT
10 32 reviews

Magical Woodland Getaway

apartment, Warren
Charming Sharon Dwelling W/ Deck & Fire Pit! - Kent, CT
9.4 10 reviews

Charming Sharon Dwelling W/ Deck & Fire Pit!

apartment, Sharon

Our Favorite 5-Star Vacation Rentals in Kent, CT

Stay in a luxury city-center vacation rental in Kent, CT for a sophisticated urban escape with premium 5-star amenities.

The House On High Meadow Farm - Kent, CT
10 23 reviews

The House On High Meadow Farm

apartment, Sharon

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.

Hidden Gem Steps To Town W/ Pool/deck/grill/sonos - Kent, CT
9.6 50 reviews

Hidden Gem Steps To Town W/ Pool/deck/grill/sonos

apartment, New Milford
Unique Geodesic Dome Escape In Nature! - Kent, CT
10 5 reviews

Unique Geodesic Dome Escape In Nature!

house, Warren
Best Location! 2hrs Nyc "Melius 5br" Poshpadsct 5* - Kent, CT
9.8 32 reviews

Best Location! 2hrs Nyc "Melius 5br" Poshpadsct 5*

apartment, Warren
Cozy Kent Loft In The Mountains - Kent, CT
No reviews

Cozy Kent Loft In The Mountains

apartment, Kent

Search Vacation Rentals with Swimming Pool in Kent, CT

Choose a Kent, CT rental with a pool for a refreshing swim right in the heart of the city.

1 Bed Pond Cottage W/ Pool/hot Tub/sauna Access - Kent, CT
9.8 110 reviews

1 Bed Pond Cottage W/ Pool/hot Tub/sauna Access

apartment, Kent
Charming Country House With Pool, Hottub & Gardens - Kent, CT
10 18 reviews

Charming Country House With Pool, Hottub & Gardens

house, Washington
Best Town, Location! 1.5hr Nyc, Calhoun Poshpadsct - Kent, CT
9.8 13 reviews

Best Town, Location! 1.5hr Nyc, Calhoun Poshpadsct

apartment, Washington
Very Best Home, Town, Restaurants, Shops 1.5hr Nyc - Kent, CT
9.9 14 reviews

Very Best Home, Town, Restaurants, Shops 1.5hr Nyc

apartment, Washington

Explore Vacation Rentals with Jacuzzi in Kent, CT

Unwind after a day of urban exploration with a private hot tub at your own vacation rental in Kent, CT.

Besttown/dine/location 1.5hrnyc ! Poshpadsct-kirby - Kent, CT
9.7 27 reviews

Besttown/dine/location 1.5hrnyc ! Poshpadsct-kirby

apartment, Washington
Fabulous Year Round Waterfront Retreat On Lake Waramaug - Kent, CT
10 7 reviews

Fabulous Year Round Waterfront Retreat On Lake Waramaug

apartment, Washington
Strawberry Ridge Chalet With Hot Tub & Sauna! - Kent, CT
9.2 29 reviews

Strawberry Ridge Chalet With Hot Tub & Sauna!

apartment, Warren
Artistic Barn: Wood Burning Hottub, Sauna And Pizza Oven - Kent, CT
9.4 6 reviews

Artistic Barn: Wood Burning Hottub, Sauna And Pizza Oven

apartment, Kent
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