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Kent vacation rentals

We found 240 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Kent that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a washer and dryer. No matter what you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about Kent

Why visit Kent

  • Outdoor Adventures: Enjoy scenic hikes and explore local state parks, perfect for nature lovers.
  • Serene Lakeside Relaxation: Unwind by the tranquil lakes, offering a peaceful escape.
  • Cultural Exploration: Discover local history through nearby museums and cultural sites.
  • Charming Accommodations: Choose from cozy cottages and stylish apartments that enhance your stay.
  • Picturesque Towns: Explore the charming nearby towns and their beautiful landscapes.

Popular types of accommodation in Kent

Planning a getaway to Kent? The excitement begins with selecting your perfect accommodation. Discover a range of options including charming houses, cozy cottages, and stylish apartments. Whether you're looking for a king bedroom, a queen bed, or a lovely garden cottage, Kent offers some of the best rentals to suit your needs. Enjoy your stay while experiencing the beauty and charm of this wonderful destination.

  • Houses: The top choice for visitors in Kent, these homes offer spacious and comfortable accommodations perfect for families or groups.
  • Cottages: A charming option, cottages provide a cozy atmosphere ideal for a romantic getaway or a peaceful retreat.
  • Apartments: Convenient and versatile, apartments are great for travelers looking for a home-like experience in the heart of Kent.
  • Cabins: Rustic and inviting, cabins offer a unique escape into nature, perfect for those seeking tranquility.
  • Agritourism: Experience rural life with agritourism stays, where you can enjoy the beauty of the countryside and local farming.**

Top attractions in and around Kent

Kent, Connecticut, offers a delightful mix of outdoor adventure and cultural exploration, making it perfect for a romantic getaway. Visitors can enjoy scenic hikes in local state parks, relax by the lake, or delve into history at nearby museums. Additional attractions include picnic shelters for a countryside escape, and nearby shopping centers for a bit of retail therapy. Whether you're seeking adventure or tranquility, Kent has something to offer every traveler.

  • Macedonia Brook State Park: A hidden gem within Kent, this state park offers stunning natural scenery, perfect for hiking and exploring. Enjoy a mix of adventure and tranquility surrounded by lush forests and beautiful vistas.
  • Bull's Bridge: This historic monument showcases the rich cultural heritage of the area. With its picturesque stone arch and scenic surroundings, it's an ideal spot for photography and appreciating local history.
  • Lake Waramaug: Located 6 miles from Kent, this lovely lake features serene beaches and a romantic atmosphere. Perfect for picnics, swimming, or simply taking in the breathtaking views.

Things to do recommended for couples

For a romantic getaway in Kent, explore the scenic trails at Kent Falls State Park, where you can enjoy a picturesque hike and breathtaking waterfalls. Consider a wine tasting at a local vineyard, or relax with a cozy dinner at a charming restaurant, perfect for couples seeking intimacy.

Things to do recommended for families

Families visiting Kent can enjoy a day at the scenic Kent Falls State Park, where kids can hike to stunning waterfalls. The nearby Kent Historical Society offers engaging exhibits, and the local shops provide charming family-friendly experiences with unique finds.

Things to do recommended for groups

Groups visiting Kent, Connecticut, can enjoy a guided hike through the scenic Kent Falls State Park, explore the charming local shops and galleries, and take part in wine tastings at nearby vineyards for a delightful taste of the region.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Kent

When traveling with a group, family, pets, or planning for an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Kent with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Kent with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kent: For many families, a vacation isn’t truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kent: If you're searching for vacation rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Kent

Kent, Connecticut, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway or a family-friendly vacation. Nearby attractions include the charming towns and picturesque landscapes that invite exploration. For a serene retreat, consider visiting the tranquil parks or indulging in the local culture. Whether you're seeking historical experiences or a relaxing escape, Kent and its neighboring areas promise an unforgettable travel experience.

  • South Kent: South Kent is a charming city located a mere 3 miles from Kent, offering an ideal outdoor escape for nature lovers and couples seeking a romantic getaway. This picturesque area is known for its stunning scenery, perfect for hiking and enjoying the fresh air. Visitors can indulge in skiing activities at nearby ski fields during the winter months, while the summer invites exploration of local lakes and nature reserves. Notable landmarks include serene lakes, beautiful nature reserves, and historical monuments, making South Kent a delightful destination for those looking to connect with nature and enjoy outdoor adventures.
  • New Milford: Situated 11 miles from Kent, New Milford boasts a vibrant atmosphere filled with opportunities for outdoor exploration and relaxation. Travelers flock to this city for its scenic beauty, romantic spots, and bustling public markets. The recreational areas offer a perfect blend of relaxation and adventure, whether you’re kayaking on the lake or enjoying a leisurely stroll through the parks. Highlights include the nearby national state park, pristine beaches, and a variety of local markets, making New Milford a wonderful stop for those looking to immerse themselves in the local culture and natural beauty.
  • Dover Plains: Just 5 miles from Kent, Dover Plains is an inviting city that offers a unique blend of outdoor activities and scenic landscapes. Known for its romantic ambiance and educational opportunities, this area is perfect for travelers interested in both adventure and learning. Outdoor enthusiasts can enjoy skiing at local fields in the winter or take in the breathtaking views of the mountains and lakes during the warmer months. Key attractions include a local stadium and the surrounding natural beauty, making Dover Plains a great choice for those seeking a memorable getaway.

Best time to go to Kent

If you're planning a trip to Kent, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in January, July and September, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.6°F (-3.0°C)Light RainMostly SunnyModerately HighSlightly Low
February28.4°F (-2.0°C)Light RainMostly CloudyModerately LowAverage
March36.0°F (2.2°C)Light RainMostly CloudyAverageSlightly Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageSlightly Low
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
August71.1°F (21.7°C)Light RainMostly SunnyAverageSlightly High
September64.0°F (17.8°C)Light RainMostly SunnyModerately HighAverage
October52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
November40.6°F (4.8°C)Light RainMostly SunnyModerately LowAverage
December32.7°F (0.4°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Planning a trip and want to save some money? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that meets your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly area where you can easily create new trips, resume your planning, or organize your travel details. You’ll see your saved or booked properties neatly sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

A New England escape in Kent

Choose a Kent vacation rental for a quintessential New England vacation just 90 miles north from New York City and 50 miles from the Connecticut coastline. Kent vacation rentals range from contemporary clapboard homes with secluded lakefront locations to sprawling refurbished farmhouses in idyllic woodland settings. Get away from it all and enjoy the lakes and mountains in this secret corner of Connecticut. In summer, local lakes and rivers are idyllic fishing and birdwatching locations, while numerous hiking and biking trails offer tantalizing views of local lakes and mountains. Then, in winter, the snowy trails are popular for sledding, snowshoeing and Nordic skiing.

Explore Hudson Valley attractions from Kent

Kent is home to one of the few remaining covered bridges in Connecticut, Bulls Bridge. It also boasts an interesting local museum dedicated to antique machinery, which features old narrow-gauge railway exhibits, mining equipment, including local rocks and minerals, and steam-powered engines. It's possible to explore the many historic sites along the Hudson Valley from your Kent vacation rental, including West Point, the Hudson Highlands and Poughkeepsie. If you venture over the state line to explore, don't miss sampling the delights of the tasting rooms and vineyards of the Hudson Valley Wine Trails.

Outdoorsy escapades in Kent

Kent Falls State Park is local gem, with gushing waterfalls among woodland. Anglers can fish for trout in its waters, while nearby Macedonia Brook State Park has miles of forested mountain trails which offer wonderful views over the Catskills. The Kent boundary pushes right up to the New York state line where a section of the Appalachian Trail can be discovered. Outdoorsy adventurers will also relish the 95-acre Lake Waramaug State Park, which has hiking trails, a small beach and a lakeside picnic area. On warm sunny days, the sparkling lake becomes a haven for canoeists, kayakers and anglers.

Kent's seasonal delights

With summer high temperatures pushing into the 80s and freezing winter months, you're treated to the full force of all 4 seasons in Kent. Spring is wonderful, with the lakeside trails awakening to the sounds of birdsong and springtime wildflowers beginning to bloom. In summer, the town hosts an annual community art event with the stores, galleries and restaurants on Main Street all offering special events. Fall is a spectacular time to visit as the forested hillsides are gilded in their autumnal finery. The annual Kent Pumpkin Run is one of the oldest races in Connecticut, bringing visitors to town to cheer on the runners while admiring the colorful fall foliage.

Exploring the natural landscape of Kent

Whether you're an active traveler or just want to spend some time taking in the scenery, Kent is a great spot to appreciate mother nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Kent Falls State Park (4.7 mi / 7.6 km)
  • Lake Waramaug State Park (4.9 mi / 7.9 km)
  • Lake Waramaug (6.3 mi / 10.1 km)
  • Steep Rock Preserve (10.6 mi / 17 km)
  • Mohawk Mountain State Park (11 mi / 17.7 km)
  • Mohawk Mountain State Forest (11.6 mi / 18.7 km)

Traveling to and around Kent

Fly into Stewart Intl. Airport (SWF), the closest airport, located 35.1 mi (56.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 24.3 mi (39.2 km) away.

Frequently asked questions

What is the best area to stay in Kent, Connecticut, United States of America when booking a vacation rental?
When looking for a great area to stay in Kent, Connecticut, you'll find that the charming downtown area offers a delightful experience for vacationers. This neighborhood is known for its picturesque scenery and close-knit community feel. One of the top attractions here is the Kent Falls State Park, where visitors can enjoy beautiful hiking trails and stunning waterfalls, superb for nature lovers and outdoor enthusiasts. Additionally, the area boasts art galleries and unique shops, making it an inviting space to explore.

Another appealing option is the area surrounding Lake Waramaug, which offers a tranquil setting with opportunities for kayaking, picnicking, and enjoying the beautiful views of the water. This region is particularly lovely during the fall when the foliage transforms into vibrant colors. In terms of vacation rentals, you'll find a variety of cozy cottages and charming homes that provide a superb base for your adventures in this scenic part of Connecticut.
How much does it cost to rent a vacation home in Kent?
Prices for vacation rentals in Kent vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Kent to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Kent vacation house rentals?
You can find great discounts on house rentals in Kent on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Kent ski resort rentals?
For ski resort rentals near Kent, Connecticut, travelers should consider the nearby Mohawk Mountain Ski Area, located just a short drive away. This area offers a range of vacation rentals in the charming towns of Kent and Cornwall, where visitors can find cozy cabins and spacious homes that cater to winter sports enthusiasts. Many of these properties are equipped with comfortable living areas, fireplaces, and fully stocked kitchens, providing the ideal setting for relaxing after a day on the slopes.

In Kent, the local ambiance is enhanced by picturesque views of the surrounding hills and the Housatonic River, making it an attractive destination year-round. Rentals here often feature outdoor spaces such as decks or patios where guests can take in the serene landscape. Additionally, some homes may offer amenities like hot tubs or game rooms, adding to the overall experience of a winter getaway.

Nearby, the town of Cornwall also has attractive options, with vacation homes that provide easy access to both Mohawk Mountain and local hiking trails, ideal for those who enjoy outdoor adventures beyond skiing. These accommodations often have rustic charm, with wood-beamed ceilings and spacious layouts, making them suitable for families or groups looking for a cozy retreat in the heart of the Litchfield Hills.
What is the most popular type of vacation rental accomodation in Kent?
In Kent, vacation houses are quite popular, with several available throughout the area. These properties typically offer spacious rooms, making them ideal for families or groups looking to enjoy the scenic beauty of the Litchfield Hills. Most vacation houses come equipped with amenities such as multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing or dining al fresco. Additionally, there are several apartments available, which provide a more compact and convenient option for couples or solo travelers. These apartments typically feature essential amenities like kitchen facilities and comfortable living areas, allowing for a cozy stay in this charming town.
Are there any family house rentals in Kent?
In Kent, Connecticut, there are several family-friendly house rentals available that cater to travelers seeking a comfortable stay. The area is known for its picturesque landscapes and outdoor activities, making it a great destination for families. Many of these homes feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can play or enjoy a barbecue.

Visitors can explore nearby attractions such as the scenic Kent Falls State Park, which offers beautiful hiking trails and stunning waterfalls, great for a family day out. Additionally, the charming downtown area has local shops and restaurants, providing opportunities to experience the town's unique character.
Can I rent a vacation home with a pool or hot tub in Kent?
In Kent, Connecticut, there are several vacation homes available for rent that come equipped with pools and hot tubs. Nestled in the picturesque Litchfield Hills, Kent offers a serene escape, great for relaxation and recreation. Travelers can expect amenities such as private swimming pools, outdoor patios for lounging, and hot tubs ideal for unwinding after a day of exploring the area's natural beauty. Many of these rentals are set in scenic locations, providing a tranquil atmosphere that complements the outdoor lifestyle. Additionally, properties often feature fully equipped kitchens and spacious living areas, making them suitable for families or groups seeking a comfortable retreat.
Can I find long-stay vacation rentals in Kent?
A long-stay vacation rental in Kent is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Kent?
In Kent, Connecticut, travelers will find several pet-friendly house rentals that offer a comfortable and inviting atmosphere for those traveling with their furry companions. The region is known for its picturesque landscapes, including the scenic Kent Falls State Park, where visitors can explore walking trails and enjoy the natural beauty of cascading waterfalls. Many vacation rentals in this area come equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them great for families or groups.

Additionally, the charming downtown area features pet-friendly cafes and shops, providing options for dining and leisure while accommodating pets.
Are there any remote work vacation rentals in Kent?
In Kent, Connecticut, there are several vacation rentals available that cater to remote workers. Many of these properties offer essential amenities such as free Wi-Fi, allowing for seamless connectivity during your stay. You can expect comfortable living spaces designed for productivity, with dedicated work areas in some units.

The town is surrounded by beautiful natural landscapes, including the nearby Kent Falls State Park, which is great for outdoor breaks and relaxation after work hours. The quaint downtown area offers charming shops and cafes, adding to the appeal of working remotely in this picturesque setting. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Kent vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Kent with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Kent?
In Kent, popular vacation rental amenities include kitchens, which allow travelers to prepare their own meals, and fireplaces that create a cozy atmosphere, especially during cooler months. Many rentals also feature coffee and tea makers for a convenient morning routine. Outdoor spaces are common, with decks or patios providing a great spot to relax and enjoy the natural surroundings. Additionally, travelers can expect basic necessities like paper towels, ensuring a comfortable and practical stay.
When is the best time to visit Kent for a vacation rental?
The best time to book a vacation rental in Kent is during the peak season from July to September. This vibrant period attracts visitors looking to enjoy the area's lush landscapes, outdoor activities, and charming small-town atmosphere. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, it's a superb time for hiking in the nearby state parks or canoeing on the scenic Housatonic River.

July stands out as the most popular month, offering a lively option with various local festivals and events that celebrate the region's culture. Travelers can immerse themselves in the natural beauty of Kent while enjoying a robust calendar of summer activities, from farmers' markets to art fairs.

For those seeking a more budget-friendly option, consider visiting in December. While this is the low season, Kent transforms into a picturesque winter wonderland, ideal for cozy getaways. You can relish the tranquility of the snow-covered landscape and warm up in local cafes or enjoy winter hikes with fewer crowds.

Ultimately, the best time to visit Kent depends on your preferences—whether you desire the energetic summer vibe or the peaceful charm of winter.
How early should I book a Kent vacation rental?
Book your Kent vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Kent, Connecticut, United States of America?
In Kent, Connecticut, visitors can enjoy a range of attractions that highlight the area's natural beauty and cultural offerings. The scenic Kent Falls State Park is a must-visit, featuring stunning waterfalls and picturesque hiking trails. The park provides a beautiful backdrop for outdoor activities and is a popular spot for photography.

The charming Kent Village is home to quaint shops and cafes, where travelers can relax and experience local culture. The Kent Art Association, located in a historic building, showcases works from local artists and frequently hosts exhibitions throughout the year.

For those interested in history, the nearby Bulls Bridge is an iconic covered bridge that offers a glimpse into the region's past and provides a lovely setting for a leisurely stroll. Additionally, the Appalachian Trail runs through the area, providing ample opportunities for hiking and enjoying the stunning views of the Litchfield Hills.
Can I change or cancel my Kent home rental booking on Vrbo?
To find Kent vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Kent vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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