Kent vacation rentals

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Top-rated vacation rentals in Kent

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Kent

4.93 out of 5 average rating, 127 reviews

Loft 22

Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*

Dec 6 – 13

$136 per night

Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Sep 6 – 13

$144 per night

Guest favorite

Vacation home in Warren

4.99 out of 5 average rating, 111 reviews

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

Jun 9 – 16

$211 per night

Guest favorite

Apartment in Litchfield

4.98 out of 5 average rating, 118 reviews

Litchfield Hills Hideaway

Enjoy the Litchfield Hills from this newly renovated one bedroom apartment with private entrance. Amenities include full kitchen, living room, bedroom with queen bed, and full en suite bathroom. WiFi and cable TV included. All located less than 2 miles from historic Litchfield Center. Our property borders on the White Memorial Foundation nature preserve, with over 40 miles of hiking trails. Mohawk Mountain Ski area in Cornwall and Ski Sundown in New Hartford are only a short drive away.

Nov 22 – 29

$120 per night

Guest favorite

Guest suite in Sherman

4.98 out of 5 average rating, 134 reviews

Cozy Scenic New England country retreat w/ hiking

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey or bike (2 bikes provided) along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian trail & other great hiking. Pets welcome. Inquire about min stay requirements.

Apr 19 – 26

$132 per night

Guest favorite

Cabin in New Milford

4.95 out of 5 average rating, 146 reviews

The Cottage on Babbling Brook

Cozy, rustic cottage. Beautifully overlooking Wimsink Brook, with 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.

Nov 29 – Dec 6

$206 per night

Guest favorite

Guest suite in Dover Plains

4.91 out of 5 average rating, 262 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Thunder Ridge ski mountain and Daryl Hall’s bar only 15 mins away. Take a ride to near-by towns (Kent, Millbrook, Amenia, Wassaic) for great food, coffee shops, antiques, parks, breweries and vineries.

Jul 9 – 16

$129 per night

Guest favorite

Farm stay in Kent

4.87 out of 5 average rating, 261 reviews

(°) The Wandering Peacock (°)

The Wandering Peacock has lots to offer guests. One can experience our outdoor spa, with a cedar hot tub and views of the Appalachian trail, or our wood burning suanna with herbs from the garden. The house showcases vintage machinery, a library, outdoor kitchen with a pizza oven and much more. Nestled within the forest foot hills of the Appalachia trails this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, local river, and waterfalls.

Mar 16 – 23

$246 per night

Superhost

Cottage in Kent

4.88 out of 5 average rating, 149 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

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

Jul 2 – 9

$339 per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Jan 23 – 30

$104 per night

Guest favorite

Home in Cornwall

4.92 out of 5 average rating, 225 reviews

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

Dec 29 – Jan 5

$201 per night

Guest favorite

Apartment in Millbrook

4.93 out of 5 average rating, 205 reviews

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

Aug 7 – 14

$111 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Kent vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Kent's top sights

Kent Falls State Park121 locals recommend

Lake Waramaug State Park29 locals recommend

Bulls Covered Bridge27 locals recommend

Kent Coffee & Chocolate Co.18 locals recommend

Macedonia Brook State Park24 locals recommend

Kent Pizza Garden8 locals recommend

Other great vacation rentals in Kent

Guest favorite

Vacation home in Torrington

4.97 out of 5 average rating, 131 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Dec 28 – Jan 4

$138 per night

Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 264 reviews

Relaxing secluded stay with loving social animals.

Sep 1 – 8

$140 per night

Guest favorite

Dome in Cornwall

4.94 out of 5 average rating, 127 reviews

Vibrant, secluded dome home in Litchfield County!

Nov 5 – 12

$291 per night

Guest favorite

Cottage in Goshen

4.98 out of 5 average rating, 103 reviews

Country Cottage in Goshen

Dec 29 – Jan 5

$119 per night

Guest favorite

Apartment in Stanfordville

4.95 out of 5 average rating, 152 reviews

Country Apartment great for a romantic getaway

Jun 25 – Jul 2

$120 per night

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 162 reviews

Lrg Studio Apartment - walk to Taft

Sep 15 – 22

$62 per night

Guest favorite

Cottage in Cornwall

4.94 out of 5 average rating, 115 reviews

Newly Built Cottage in Housatonic Valley

Dec 24 – 31

$192 per night

Guest favorite

Apartment in Millerton

4.8 out of 5 average rating, 230 reviews

Gardens Galore and Village Whimsy Retreat

Jul 13 – 20

$89 per night

Show all

Other great vacation rentals in Kent

Guest favorite

Guesthouse in Sharon

5.0 out of 5 average rating, 64 reviews

Cottage with a Waterfall View

Sep 26 – Oct 3

$94 per night

Guest favorite

Home in Cornwall

4.98 out of 5 average rating, 51 reviews

The Brookside Barn

Sep 27 – Oct 4

$140 per night

Guest favorite

Apartment in Amenia

5.0 out of 5 average rating, 22 reviews

Amenia Main St Cozy Studio

Jul 31 – Aug 7

$67 per night

Guest favorite

Home in Kent

4.94 out of 5 average rating, 52 reviews

Cheerful 2-bedroom house porch and fireplace

Sep 6 – 13

$152 per night

Guest favorite

Home in Kent

4.95 out of 5 average rating, 20 reviews

Cozy Spring Getaway

Dec 14 – 21

$177 per night

Guest favorite

Home in Kent

5.0 out of 5 average rating, 12 reviews

Charming Home in Kent

Aug 29 – Sep 5

$170 per night

Guest favorite

Cottage in Kent

5.0 out of 5 average rating, 33 reviews

Cheerful one-bedroom cottage with large porch

Aug 27 – Sep 3

$180 per night

Guest favorite

Home in Cornwall

5.0 out of 5 average rating, 16 reviews

The Farmhouse

Sep 19 – 26

$173 per night

Show all

Quick stats about vacation rentals in Kent

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
2.5K reviews

Frequently Asked Questions

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 pet-friendly vacation rentals in Kent?
Four-legged friends are welcome in Kent. Choose from more than 30 vacation rentals for guests traveling with pets.
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!
Do house rentals in Kent have wifi?
Absolutely! We offer over 20 house rentals with wifi in Kent. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Kent?
Kent has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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.
How much does it cost to stay in house rentals in Kent?
Experience the best of Kent with our house rentals, starting at about $80 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 20 house rentals with air conditioning in Kent. Enjoy a tailored experience with all the comforts you desire.

Kent vacation rentals

Top-rated vacation rentals in Kent

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Kent vacation rentals

Stay near Kent's top sights

Other great vacation rentals in Kent

Vacation home in Torrington

Farm stay in Ancram

Dome in Cornwall

Cottage in Goshen

Apartment in Stanfordville

Guest suite in Watertown

Cottage in Cornwall

Apartment in Millerton

Other great vacation rentals in Kent

Guesthouse in Sharon

Home in Cornwall

Apartment in Amenia

Home in Kent

Home in Kent

Home in Kent

Cottage in Kent

Home in Cornwall

Quick stats about vacation rentals in Kent

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Kent?

Are there pet-friendly vacation rentals in Kent?

Are there Kent vacation rentals on Airbnb with pools?

Do house rentals in Kent have wifi?

Are there family-friendly house rentals in Kent?

Do house rentals in Kent have a bbq area?

How much does it cost to stay in house rentals in Kent?

Do house rentals in Kent have air conditioning?

Destinations to explore