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.*

Mar 4 – 11

G$32,221 GYD 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.

Oct 10 – 17

G$35,300 GYD per night

Guest favorite

Vacation home in Warren

4.99 out of 5 average rating, 112 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

Jul 26 – Aug 2

G$72,799 GYD per night

Guest favorite

Vacation home in Torrington

4.96 out of 5 average rating, 133 reviews

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

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

Jan 25 – Feb 1

G$33,190 GYD 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.

Jan 15 – 22

G$32,180 GYD per night

Guest favorite

Cottage in Goshen

4.98 out of 5 average rating, 103 reviews

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Oct 23 – 30

G$28,559 GYD per night

Superhost

Cottage in Kent

4.88 out of 5 average rating, 151 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

Aug 31 – Sep 7

G$82,164 GYD 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.

Sep 4 – 11

G$25,305 GYD per night

Guest favorite

Home in Cornwall

4.92 out of 5 average rating, 227 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

Nov 19 – 26

G$47,786 GYD per night

Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 264 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door.

Aug 24 – 31

G$35,891 GYD 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. .

Jul 12 – 19

G$26,905 GYD per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 342 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Oct 1 – 8

G$19,532 GYD 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

Kent Pizza Garden8 locals recommend

Macedonia Brook State Park24 locals recommend

Other great vacation rentals in Kent

Guest favorite

Apartment in Litchfield

4.98 out of 5 average rating, 119 reviews

Litchfield Hills Hideaway

Oct 14 – 21

G$28,760 GYD per night

Guest favorite

Cabin in New Milford

4.95 out of 5 average rating, 148 reviews

The Cottage on Babbling Brook

Aug 6 – 13

G$55,727 GYD per night

Guest favorite

Loft in Stanfordville

4.99 out of 5 average rating, 101 reviews

Harley's Hideaway - Cozy Furnished Apartment

Nov 7 – 14

G$28,645 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 742 reviews

Hudson Valley Tiny House

Jul 13 – 20

G$22,914 GYD per night

Guest favorite

Home in Pawling

5.0 out of 5 average rating, 186 reviews

Hobbit House of Pawling

Jul 24 – 31

G$119,484 GYD per night

Guest favorite

Apartment in Stanfordville

4.95 out of 5 average rating, 153 reviews

Country Apartment great for a romantic getaway

Nov 13 – 20

G$28,550 GYD per night

Guest favorite

Dome in Cornwall

4.94 out of 5 average rating, 129 reviews

Vibrant, secluded dome home in Litchfield County!

Nov 11 – 18

G$72,653 GYD per night

Guest favorite

Apartment in Dover Plains

4.95 out of 5 average rating, 138 reviews

*The Ridge House*

Sep 15 – 22

G$35,520 GYD per night

Show all

Other great vacation rentals in Kent

Guest favorite

Apartment in Amenia

5.0 out of 5 average rating, 22 reviews

Amenia Main St Cozy Studio

Aug 27 – Sep 3

G$16,028 GYD per night

Guest favorite

Home in Kent

4.94 out of 5 average rating, 52 reviews

Cheerful 2-bedroom house porch and fireplace

Nov 18 – 25

G$36,692 GYD per night

Guest favorite

Home in Cornwall

4.98 out of 5 average rating, 52 reviews

The Brookside Barn

Jan 28 – Feb 4

G$33,315 GYD per night

Guest favorite

Home in Kent

5.0 out of 5 average rating, 13 reviews

Charming Home in Kent

Sep 15 – 22

G$41,162 GYD per night

Guest favorite

Guesthouse in New Milford

5.0 out of 5 average rating, 43 reviews

Luxury in the Litchfield Hills

Sep 29 – Oct 6

G$43,777 GYD per night

Guest favorite

Cottage in Kent

5.0 out of 5 average rating, 33 reviews

Cheerful one-bedroom cottage with large porch

Sep 12 – 19

G$42,825 GYD per night

Guest favorite

Home in Kent

4.95 out of 5 average rating, 20 reviews

Cozy Spring Getaway

Dec 16 – 23

G$42,806 GYD per night

Guest favorite

Home in Cornwall

5.0 out of 5 average rating, 20 reviews

The Farmhouse

Oct 10 – 17

G$41,081 GYD 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

Apartment in Litchfield

Cabin in New Milford

Loft in Stanfordville

Tiny home in New Paltz

Home in Pawling

Apartment in Stanfordville

Dome in Cornwall

Apartment in Dover Plains

Other great vacation rentals in Kent

Apartment in Amenia

Home in Kent

Home in Cornwall

Home in Kent

Guesthouse in New Milford

Cottage in Kent

Home 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