Vacation rentals with a kayak in Litchfield County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Litchfield County

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Guest favorite

Home in Brookfield

4.98 out of 5 average rating, 121 reviews

Stay at Old Dorset Farm & create lifelong memories

This 1905 Historic Old Bakery is the perfect location to create lifelong memories while exploring quaint New England. Set on 4 acres, with a lake, trails and golden rolling hills just minutes away, you’ll enjoy all of New England's beauty. Hiking, kayaking, antiques shopping or gallery visiting... it can all be done right here. But you don't have to go anywhere. The two fireplaces invite you to just stay, relax and enjoy the complimentary bottle of Prosecco. Follow us on Insta: @Old_Dorset_Farm

Dec 12 – 19

R6,729 ZAR per night

Guest favorite

Home in Harwinton

4.97 out of 5 average rating, 62 reviews

Direct Waterfront with Private Beach - Entire Home

Rare opportunity to enjoy DIRECT WATERFRONT living, great for your next vacation, relaxing weekend, or to work remotely. Fully furnished and completely remodeled home includes all amenities, complete kitchen and accessories, washer/dryer, central air, large deck, fast WiFi, Smart TVs. Featuring beach, swimming, kayaking, canoeing, paddle boarding, biking, skating and fishing. Enjoy spectacular views of the lake from the open concept home We are a SUPERHOST - Nearly 90% booked, so book early

Jul 16 – 23

R7,175 ZAR per night

Guest favorite

Guesthouse in Litchfield

5.0 out of 5 average rating, 14 reviews

Bantam Woods Retreat - 2 bedrooms with queen beds

Brand new stand alone guest house. Nestled in the six acre woods, river frontage. Near downtown Bantam. Near Taft, Kent, Gunn, Rumsey Hall, Forman schools, great restaurants (Arethusa, Materia), shopping, galleries, antique shops. Hike at White Memorial, Hidden Valley Preserve, Mt. Tom. From Lynda: "Laurie’s stand-alone guest house was impeccable. Felt like we were the first ones to stay. Top quality appointments, serene setting. Just what the Dr ordered. We will return for sure. Super host".

Sep 26 – Oct 3

R4,208 ZAR per night

Guest favorite

Bungalow in Plymouth

4.97 out of 5 average rating, 64 reviews

Lakefront Bungalow Bliss - 2BR Cottage

Unwind by a crackling fire on the lake at dusk. Bungalow Bliss offers expansive lakefront views from its many unique outdoor spaces. Situated in a tranquil private Lake community, this home is ideal for swimming, fishing, kayaking, bird watching and skating in wintertime. Enjoy your next getaway, relaxing couples weekend, or just working remotely in a peaceful, centered home. This well-equipped home is located near wineries, golf courses and hiking in the Litchfield hills. We're Pet-Friendly

Oct 14 – 21

R10,199 ZAR per night

Guest favorite

Home in Morris

4.87 out of 5 average rating, 142 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Jan 29 – Feb 5

R7,701 ZAR per night

Guest favorite

Cabin in Bethlehem

4.91 out of 5 average rating, 11 reviews

Swim, fish, kayak & RELAX!

Non- smoking cottage sleeps six (6). 1st floor queen bedroom, 2nd floor two lofts with two twin beds in each. Linens, towels, dishes, bathroom essentials, Keurig, & full kitchen. 2 kayaks, small row boat, life-jackets, fire pit, gas grill, games, corn hole, badminton. WiFi, streaming TV. Heat, AC and ceiling fans. Access to the lake and private beach. Local wineries, antique shops, and farms nearby. Bethlehem Fair, Garlic Fest and CT agricultural fairs. Great fall color and amazing Stars.

May 2 – 9

R4,346 ZAR per night

Guest favorite

Cabin in Colebrook

4.95 out of 5 average rating, 75 reviews

Cozy cabin with beach on pond with 7 acres!

Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Huge yard right on pond. Small simple rooms, woodstove and all the comforts of home. 2 acre pond u can swim, fish, canoe, kayak or bring a float! On a quiet back road you can walk, run or bike to local trails or stay and walk the trails around the pond or have a small fire outside in firepit! Clean and cozy house surrounded by nature on 7 acres! Rent weekly/monthly! Great WIFI! Close to ski resorts and dispensaries!

Dec 13 – 20

R4,441 ZAR per night

Guest favorite

Home in Goshen

5.0 out of 5 average rating, 46 reviews

Superb Lakefront Getaway with Family and Friends

YellowBird welcomes guests with luxury vaca vibes + gorgeous water and sunset views on friendly Woodridge Lake, just minutes from Litchfield County’s charming small towns, golf, hikes + ski resorts. -2 hrs NYC, 2.5 hrs Boston, only 10 min from Litchfield village center -Gorgeous & fun all year -Enjoy 150 ft of lakefront, swimming, fishing, parks, golf, hiking, mountain and countryside vistas, foliage, covered bridges, antiquing, vineyards, top restaurants, cultural activities & skiing

Oct 21 – 28

R16,737 ZAR per night

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 310 reviews

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, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Mar 28 – Apr 4

R8,451 ZAR per night

Guest favorite

Guesthouse in Morris

4.94 out of 5 average rating, 34 reviews

Peaceful Year Round Lakehouse

Kick back and relax in this calm, stylish space. Bantam Lake Gem; private walk in beach with kayaks, fishing poles and floats. 2 story open floor plan. 2 bedrooms/1 bath. Large beautiful deck. Countless hiking trails. Town of Litchfield Connecticut, plenty of eateries, county fairs etc. Beautiful western exposure, picture perfect sunsets all year round Ice fishing 🎣 in the winter, nearby ski slopes ⛷, concert venues, breweries and shopping

Feb 16 – 23

R5,175 ZAR per night

Guest favorite

Home in Bethlehem

4.94 out of 5 average rating, 33 reviews

The Bethlem Lake House, Lake Side Relaxation!

Private lake house on peaceful Long Meadow Pond. As you look out onto the lake and listen to the songbirds in the morning, the hustle and bustle of city life feels like a far-off memory. Discover picturesque Litchfield county, take a nearby hike at White Memorial, or enjoy a refreshing dip from your own private dock. Unwind with a delicious al fresco dinner and enjoy a nightcap on the deck while watching the sunset over the lake.

Sep 15 – 22

R5,431 ZAR per night

Guest favorite

Cabin in New Fairfield

4.98 out of 5 average rating, 257 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

Named one of the best Airbnbs in CT by Business Insider, The Little Lake Cabin is the perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake. The cabin is a place to slow down and reconnect. Spend your days on the lake, exploring nearby towns, wineries & antique shops & your nights in the hot tub, by the fire pit roasting s'mores and gazing up at the stars. Find us on IG @thelittlecabins

Feb 24 – Mar 3

R5,164 ZAR per night