Kent vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Kent

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

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 11 – 18

R2,773 ZAR per night
Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 193 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.

May 8 – 15

R3,197 ZAR 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.

Feb 1 – 8

R2,612 ZAR per night

Popular amenities for Kent vacation rentals

Stay near Kent's top sights

Kent Falls State Park121 locals recommend
Lake Waramaug State Park29 locals recommend
Macedonia Brook State Park24 locals recommend
Bulls Covered Bridge27 locals recommend
Kent Coffee & Chocolate Co.18 locals recommend
Kent Pizza Garden8 locals recommend

Other great vacation rentals in Kent

Guest favorite

Apartment in Millerton

4.8 out of 5 average rating, 230 reviews

Gardens Galore and Village Whimsy Retreat

Oct 25 – Nov 1

R1,938 ZAR per night
Guest favorite

Dome in Cornwall

4.94 out of 5 average rating, 125 reviews

Vibrant, secluded dome home in Litchfield County!

Jan 22 – 29

R5,812 ZAR per night
Guest favorite

Apartment in Millbrook

4.93 out of 5 average rating, 204 reviews

Red Tail Ridge

Sep 14 – 21

R2,436 ZAR per night
Guest favorite

Cottage in Goshen

4.98 out of 5 average rating, 102 reviews

Country Cottage in Goshen

Apr 2 – 9

R2,594 ZAR per night
Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 162 reviews

Lrg Studio Apartment - walk to Taft

Aug 17 – 24

R1,361 ZAR per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Sep 14 – 21

R2,024 ZAR per night
Guest favorite

Cottage in Cornwall

4.94 out of 5 average rating, 113 reviews

Newly Built Cottage in Housatonic Valley

Jul 18 – 25

R4,201 ZAR per night
Guest favorite

Vacation home in Torrington

4.97 out of 5 average rating, 128 reviews

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

Mar 21 – 28

R3,164 ZAR per night
Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 738 reviews

Hudson Valley Tiny House

Jun 11 – 18

R2,081 ZAR per night
Guest favorite

Apartment in Stanfordville

4.95 out of 5 average rating, 151 reviews

Country Apartment great for a romantic getaway

May 14 – 21

R2,593 ZAR per night
Guest favorite

Guest suite in Canaan

4.98 out of 5 average rating, 290 reviews

Walk to Brewery in Historic Railroad Depot

Nov 29 – Dec 6

R2,687 ZAR per night
Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 305 reviews

The Cove Cabin

Dec 31 – Jan 7

R10,265 ZAR per night

Other great vacation rentals in Kent

Guest favorite

Apartment in Amenia

5.0 out of 5 average rating, 18 reviews

Amenia Main St Cozy Studio

Aug 5 – 12

R1,456 ZAR per night
Guest favorite

Home in Cornwall

4.98 out of 5 average rating, 47 reviews

The Brookside Barn

Feb 1 – 8

R3,026 ZAR per night
Guest favorite

Home in Kent

4.94 out of 5 average rating, 49 reviews

Cheerful 2-bedroom house porch and fireplace

Sep 15 – 22

R3,335 ZAR per night
Guest favorite

Home in Kent

5.0 out of 5 average rating, 12 reviews

Charming Home in Kent

May 13 – 20

R3,592 ZAR per night
Guest favorite

Guesthouse in New Milford

5.0 out of 5 average rating, 41 reviews

Luxury in the Litchfield Hills

Sep 29 – Oct 6

R3,976 ZAR per night
Superhost

Guesthouse in Dover Plains

4.88 out of 5 average rating, 82 reviews

Spilt Milk Cottage - Hudson Valley, NY

Dec 8 – 15

R2,109 ZAR per night
Guest favorite

Barn in Kent

4.89 out of 5 average rating, 65 reviews

Country Guest Cottage/Barn

Nov 3 – 10

R4,365 ZAR per night
Guest favorite

Home in Kent

4.98 out of 5 average rating, 46 reviews

Cheerful 3 bedroom Kent getaway

Sep 18 – 25

R5,410 ZAR per night
Guest favorite

Cottage in Kent

5.0 out of 5 average rating, 33 reviews

Cheerful one-bedroom cottage with large porch

Apr 29 – May 6

R3,890 ZAR per night
Guest favorite

Apartment in Litchfield

4.98 out of 5 average rating, 86 reviews

Artist's Garden Apartment

Jul 15 – 22

R2,544 ZAR per night
Guest favorite

Cottage in Pawling

5.0 out of 5 average rating, 59 reviews

Twin Lakes Designer A-frame Stone Cottage

Sep 15 – 22

R6,928 ZAR per night
Guest favorite

Guesthouse in Gaylordsville

4.98 out of 5 average rating, 90 reviews

Adorable Cottage in Pastoral Setting

Nov 20 – 27

R2,751 ZAR per night

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

20 properties allow pets

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

2.4K 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 20 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Litchfield County
  5. Kent