
Holiday houses in Kent
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Top-rated holiday rentals in Kent
Guests agree: these stays are highly rated for location, cleanliness and more.

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

Vibrant, secluded dome home in Litchfield County!
Positive vibes, tranquility and refuge await! Reconnect with nature at this unforgettable escape on 3+ acres. Allowing an open flow of light, atmosphere, and energy, dome homes can offer a spiritual experience, and this property offers all that times two. Consider these naturally efficient domes your break from it all 10 minutes or less to; Skiing (Mohawk Mt.) Lake Waramaug Appalachian Trail Housatonic River Ct Wine Trail Kent Falls Antiques, art galleries, farmers markets, brewery, & more

Private new house on 10 acres of pristine nature
Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Farm House
A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers we sell at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, chickens, barn cats and a resident farm dog, Finula. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

The Cottage on Babbling Brook
A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Luxury in the Litchfield Hills
Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

(°) The Wandering Peacock (°)
The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

NEW - Hot Tub - Mohawk Mountain - Appalachian Trail
Equipped with essentials such as air conditioning, cleaning products, cooking basics, and a dedicated workspace. Guests can prepare meals in the fully equipped kitchen, which includes dishes, silverware, and cooking utensils, dishwasher, and microwave. A washer and dryer, hair dryer, heating, and hot tub are also available for guests' use. 2 Min – Appalachian Trail 4 Min - Kent Town center 9 Min – Kent falls 10 Min - Bulls Bridge 19 Min - Mohawk Mountain Ski Area

Secluded modern forest cabin with private brook
Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin
Popular amenities for Kent holiday rentals
Other great holiday rentals in Kent

Fully Renovated Rural Barn

Beautiful Cabin in Cornwall CT.

Gunn Brook Mountain House

Cozy Hudson Valley House

Cozy house w/ fireplace close to Mohawk ski area

Guesthouse at Bantam Woods - 2 bedrooms

Airstream Forest Glamping near Metro North Train

Country retreat on 4 private acres
When is the best time to visit Kent?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $430 AUD | $430 AUD | $411 AUD | $430 AUD | $433 AUD | $418 AUD | $437 AUD | $437 AUD | $453 AUD | $444 AUD | $501 AUD | $463 AUD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Kent?
Four-legged friends are welcome in Kent. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Kent?
Yes! Work meets play with ease at over 30 vacation rentals in Kent featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Kent vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Kent, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Kent?
Kent has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in boutique hotel rentals in Kent?
Experience the best of Kent with our boutique hotel rentals, starting at about $280 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Kent have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Kent. Enjoy a tailored experience with all the comforts you desire.
Do boutique hotel rentals in Kent have wifi?
Absolutely! We offer over 10 boutique hotel rentals with wifi in Kent. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Kent have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Kent. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Kent

Total holiday rentals
Explore 80 holiday rentals in Kent

Nightly prices starting at
Kent holiday rentals start at $72 AUD per night before taxes and fees

Verified guest reviews
Over 3,140 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Kent holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Kent rentals

4.9 Average rating
Kent stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Yale University
- Fairfield Beach
- Six Flags New England
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Taconic State Park
- Mount Southington Ski Area
- Bear Mountain State Park
- Yale University Art Gallery
- Ski Sundown
- Sherwood Island State Park
- Sleeping Giant State Park
- Compo Beach
- Norman Rockwell Museum
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