Vacation rentals with a kayak in Fairfield County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Fairfield 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

Oct 2 – 9

G$74,745 GYD per night

Guest favorite

Home in Fairfield

5.0 out of 5 average rating, 11 reviews

Linda Marie’s Cozy Cottage in Lake Hills

Welcome to Linda Marie’s Cozy Cottage located in Lake Hills neighborhood of Fairfield Ct. . Enjoy easy access to everything from this perfectly located home base. You will be just blocks to numerous Restaurants and shopping, pharmacies ect. Take a tour of Sacred Heart or Fairfield University, only minutes away. Enjoy entertainment at one of our nearby arenas. You can also just relax & enjoy your morning coffee on the beautiful back deck, & listen to running water way that runs into the lake.

May 27 – Jun 1

G$96,377 GYD per night

Guest favorite

Home in Danbury

4.87 out of 5 average rating, 116 reviews

Candlewood Lakefront Retreat

This beautiful custom-built lakefront house is located only 90 min from NYC. Surrounded by nature, it is serene and peaceful. This spacious and cozy home has panoramic views from the living room, office, and master. The owners have tastefully updated throughout. If you are looking for a truly unique and peaceful retreat on the lake, come have an al fresco morning coffee, or sunset dinner while sitting outside on the deck gazing at the rippling lake. Sunrise or sunset, you will be enchanted.

May 13 – 20

G$107,826 GYD per night

Guest favorite

Home in Brookfield

5.0 out of 5 average rating, 40 reviews

Waterfront Gem: Pontoon & Private Beach

Indulge in lakeside luxury at our waterfront retreat on Candlewood Lake. A week-long rental ensures ample time for unforgettable family moments. Enjoy a 65-inch ET center w/ SONOS surround sound (inside & outside speakers), air hockey table & lawn games. Stay active with a Peloton & gym equipment. The outdoor kitchen, hot tub & outdoor shower provide al fresco delights. 4 bedrooms & 2.5 baths, our lakehouse offers comfort & convenience. Book now for a family getaway! 🌟🚤🍿🏓🚴‍♂️🌭🚿🛌

Sep 27 – Oct 4

G$233,059 GYD per night

Guest favorite

Cottage in South Salem

5.0 out of 5 average rating, 76 reviews

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine-Yoga,Canoe, Bocce, Cornhole, Swim, Hike, Grill etc

Jun 24 – Jul 1

G$61,415 GYD per night

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 311 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.

Dec 10 – 17

G$92,542 GYD per night

Guest favorite

Home in Milford

5.0 out of 5 average rating, 46 reviews

Direct Oceanfront Home

Breathtaking 4-bedroom coastal retreat with direct ocean views where the Long Island Sound becomes your backyard playground. Convenience is at your fingertips: home is located within walking distance to restaurants and town center is just a short ride away. The back patio is fully equipped with a gas grill, outdoor dining area, and stairs leading directly into the Long Island Sound- truly the perfect blend of comfort and coastal bliss!

Nov 4 – 11

G$110,399 GYD per night

Guest favorite

Home in Danbury

5.0 out of 5 average rating, 9 reviews

Candlewood Lake - Direct Access

Direct lakefront home is the perfect getaway only 90 minutes away from NYC on beautiful Candlewood Lake. 4 bedroom, 3 full bathroom plus 2 half. Plenty of space inside and out. Private and peaceful oasis has two full kitchens and an outdoor cooking space with BBQ and stone-fire pizza oven. Great big yard for outdoor fun, with ample dock space for your boat or jet-ski. Sit on the deck or fish off the dock. Direct access to the lake. Sleeps 8.

Sep 8 – 15

G$193,292 GYD per night

Superhost

Home in Port Jefferson

4.8 out of 5 average rating, 266 reviews

The Hilltop Harborview

Guests will immediately walk past spacious hot tub into a comfortable sunroom where you’ll watch the most colorful, water view sunsets Long Island has to offer! This one of a kind offers a sprawling layout that has 3 queen size bedrooms and 1 king . We can also provide an air mattress for an additional guest. There is a kitchen equipped with stove, oven, dishwasher and washer and dryer! This beautiful walking Village has so much to offer!

Jan 1 – 8

G$83,516 GYD per night

Guest favorite

Cottage in Pawling

5.0 out of 5 average rating, 62 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Nov 19 – 26

G$75,516 GYD per night

Guest favorite

Cabin in New Fairfield

4.98 out of 5 average rating, 258 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

Mar 3 – 10

G$56,036 GYD per night

Guest favorite

Home in New Fairfield

4.93 out of 5 average rating, 14 reviews

Peaceful All Season Lake Community Home

Relax with the whole family at this peaceful place to stay. 3 Bedroom, 2 Full Baths, 2 Living Rooms, Office Room, Sun Room, Large Newly Remodeled Kitchen at Heart of the Home, Dining Room, Deck on the Main Floor, Deck off the Master Bedroom, Washer & Dryer Candlewood Lake Views, Young Children Friendly, Private Beach Access, 90 mins from NYC, Safe and Peaceful Community.

Jul 31 – Aug 7

G$70,918 GYD per night