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.

Guest favorite
Apartment in Kent
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.*
Nov 7 – 14
€ 155 per night
4.93 out of 5 average rating, 127 reviews
Guest favorite
Guest suite in Bethlehem
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.
Jun 29 – Jul 6
€ 191 per night
4.99 out of 5 average rating, 193 reviews
Guest favorite
Apartment in Litchfield
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.
Jan 6 – 13
€ 151 per night
4.98 out of 5 average rating, 118 reviews

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
Gardens Galore and Village Whimsy Retreat
Oct 16 – 23Individual Host,
€ 103 per night
4.8 out of 5 average rating, 230 reviews
Guest favorite
Dome in Cornwall
Vibrant, secluded dome home in Litchfield County!
Oct 11 – 18
€ 378 per night
4.94 out of 5 average rating, 124 reviews
Guest favorite
Apartment in Millbrook
Red Tail Ridge
Jul 12 – 19Individual Host,
€ 131 per night
4.93 out of 5 average rating, 204 reviews
Guest favorite
Guest suite in Millbrook
The Haley Cabin
Nov 17 – 24Individual Host,
€ 147 per night
4.89 out of 5 average rating, 132 reviews
Superhost
Cottage in North East
Sunset Cottage: Unplug - Relax - Recharge
Nov 13 – 20Individual Host,
€ 144 per night
4.86 out of 5 average rating, 129 reviews
Guest favorite
Cabin in Sherman
The Cove Cabin
Feb 27 – Mar 6
€ 595 per night
4.97 out of 5 average rating, 303 reviews
Guest favorite
Guest suite in Watertown
Lrg Studio Apartment - walk to Taft
Jul 15 – 22Individual Host,
€ 83 per night
4.91 out of 5 average rating, 161 reviews
Guest favorite
Guest suite in Canaan
Walk to Brewery in Historic Railroad Depot
Aug 13 – 20Individual Host,
€ 152 per night
4.98 out of 5 average rating, 289 reviews
Superhost
Apartment in Litchfield
The Village Apt
Sep 15 – 22Individual Host,
€ 168 per night
4.84 out of 5 average rating, 169 reviews
Guest favorite
Cottage in Goshen
Country Cottage in Goshen
Jul 4 – 11Individual Host,
€ 153 per night
4.98 out of 5 average rating, 102 reviews
Guest favorite
Home in Warren
Litchfield County Getaway
Aug 31 – Sep 7Individual Host,
€ 341 per night
4.93 out of 5 average rating, 103 reviews
Guest favorite
Apartment in Dover Plains
*The Ridge House*
Jun 13 – 20
€ 169 per night
4.95 out of 5 average rating, 136 reviews

Other great vacation rentals in Kent

Guest favorite
Apartment in Amenia
Amenia Main St Cozy Studio
Jun 30 – Jul 7
€ 78 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Kent
Cheerful 2-bedroom house porch and fireplace
Feb 26 – Mar 5
€ 204 per night
4.94 out of 5 average rating, 48 reviews
Guest favorite
Home in Cornwall
The Brookside Barn
Dec 11 – 18Individual Host,
€ 171 per night
4.98 out of 5 average rating, 47 reviews
Guest favorite
Home in Kent
Charming Home in Kent
Apr 26 – May 3
€ 217 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Guesthouse in New Milford
Luxury in the Litchfield Hills
Sep 20 – 27
€ 219 per night
5.0 out of 5 average rating, 40 reviews
Guest favorite
Home in Kent
Cheerful 3 bedroom Kent getaway
Apr 10 – 17
€ 305 per night
4.98 out of 5 average rating, 46 reviews
Guest favorite
Guesthouse in Dover Plains
Spilt Milk Cottage - Hudson Valley, NY
Jul 12 – 19
€ 123 per night
4.88 out of 5 average rating, 82 reviews
Guest favorite
Cottage in Kent
Cheerful one-bedroom cottage with large porch
Jun 7 – 14
€ 214 per night
5.0 out of 5 average rating, 33 reviews
Guest favorite
Barn in Kent
Country Guest Cottage/Barn
May 22 – 29
€ 240 per night
4.89 out of 5 average rating, 65 reviews
Guest favorite
Apartment in Litchfield
Artist's Garden Apartment
Aug 5 – 12
€ 146 per night
4.98 out of 5 average rating, 85 reviews
Guest favorite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
Oct 22 – 29
€ 358 per night
5.0 out of 5 average rating, 59 reviews
Guest favorite
Guesthouse in Gaylordsville
Adorable Cottage in Pastoral Setting
Aug 19 – 26Individual Host,
€ 163 per night
4.98 out of 5 average rating, 90 reviews

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