Vacation rentals with a kayak in New Haven County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in New Haven County

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Guest favorite

Home in Branford

5 out of 5 average rating, 7 reviews

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot curved custom-built, direct-waterfront, home. Amazing location with water on three sides, two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, pier, kayaks, boat house, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor rooftop. Open floor plan, sweeping staircase, 5 bedrooms plus loft. So much to do and enjoy in this waterfront oasis! (Pool not heated; pool closed after mid Oct.)

Guest favorite

Home in East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Guest favorite

Place to stay in Middletown

4.96 out of 5 average rating, 46 reviews

A Luxury Estate Elegant & Private~White Lion Manor

Escape the frenzy of the world in this family friendly rental, every detail is taken care of, From the garden, saltwater pool, and courtyard views. With over 7,500 sq ft of opulent living space, White Lion Manor is more than a stay it’s a unique experience tailored for those seeking the extraordinary.The 6 person hot tub, sauna, massage chair, and endless amenities will help you Indulge in the opulence of our meticulously curated mansion and immerse yourself in the lavish lifestyle you deserve.

Guest favorite

Rental unit in Branford

4.94 out of 5 average rating, 18 reviews

Stony Crk Studio ideal for trvl nurses…

Peaceful shoreline studio/retreat for trvl nurses, grad students etc near New Haven. Single occupancy studio comprises upper east-wing of our home—has its own entrance up the exterior stairway with a dbbl-locked interior door and soundproofing for your privacy. Enjoy the balcony views and sunny chaise lounge chairs in rear-garden. Kick off your shoes and totally RELAX in our sleepy niche called Stony Creek, where the beach and harbor, food and shops & historic Thimble Islands are steps away.

Guest favorite

Home in Milford

4.93 out of 5 average rating, 14 reviews

Charming 3 bedroom Beach Front Cottage

The Fall is a great time to enjoy the solitude of the beach and watch as the tide ebbs and flows on warm days and cool nights. Have fun with the whole family, friends or loved ones at our beach front escape. Perfect for some fun in the sun. An amazing Sandbar at low-tide, a deck to relax on and a cozy inside are just a few of our great amenities. There is also a Kayak, Paddle-board and raft to enjoy. Feel free to use the fire-pit or fish off the beach. The opportunities are endless.

Guest favorite

Cottage in Branford

4.98 out of 5 average rating, 55 reviews

The Dream Location for Your Perfect Vacation

Location, location, location! Nestled at the very tip of Indian Neck and entrance of the Branford River. Recently updated, 1000 sq ft, 3 bedroom, 1.5 bath, direct water front cottage(duplex) is centrally located for whatever your needs. This is truly New Englands coastal living at its finest. This location will not disappoint. Approximate Distance - Mohegan Sun(45miles), Foxwoods(50 miles), Yale(10), NYC(70), Hospice (5), Anthonys Ocean View (7), Amarante’ Sea Cliff (7), Owenego Inn (1)

Guest favorite

Home in Oxford

4.97 out of 5 average rating, 37 reviews

Lakefront Oasis - Getaway to this Oxford Treasure!

Relax with family and friends at this breathtaking lake front home. Peaceful setting with beautiful views of Swan Lake. Updated bedrooms, completely renovated bathrooms and all new kitchen appliances. A kayak and paddleboard await your next adventure. A brand new dock was installed for boating, fishing and swimming right from our backyard. Just a few minutes from the town center grocery store, restaurants, amusement parks, skiing and more. Dogs considered on a case by case basis!

Guest favorite

Cottage in Guilford

4.99 out of 5 average rating, 96 reviews

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Guest favorite

Home in West Haven

5 out of 5 average rating, 19 reviews

Cozy beach house with gorgeous sunrises

Welcome to Anchor Haven! Make unforgettable memories at our charming newly remodeled beach cottage located within a stone's throw to the shore. Relax while enjoying the ocean views and beautiful sunrises from the two story porch. Located in a desirable, quiet neighborhood of West Haven CT and within walking distance to the beach, pizza, liquor and deli. Anchor Haven sleeps 8 guests comfortably. One bedroom and a full bathroom are located on the first level, with no stairs access.

Guest favorite

Home in Milford

5 out of 5 average rating, 77 reviews

Luxurious Oceanfront Escape With Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Guest favorite

Home in Clinton

5 out of 5 average rating, 6 reviews

Boulder Lake House Retreat

Experience the magic of fall at our beautiful lake house—an ideal retreat for families, friends, or a romantic getaway! Nestled along Boulder Lake and just under 3 miles from Hammonasset State Park, our home offers the perfect blend of comforts and adventure. Enjoy the crisp autumn air while kayaking on the lake, savor a warm cup of coffee on the deck as you take in the vibrant fall foliage, or gather around the fire pit for a cozy evening under the stars!

Guest favorite

Loft in New Haven

4.87 out of 5 average rating, 84 reviews

Cozy Fall Loft On The Water

An adorable and rustic loft right on the Quinnipiac River. Featuring all the creature comforts expected as well as smart tv, Mac computer, full kitchen and bath as well as a pull out sofa. Take in the views on the private balcony or explore the marina grounds! Feeling adventurous? Book a kayak/e-boat rental or schedule a charter tour and enjoy the Q River and Long Island sound just steps away. Sit back and relax in this perfect little getaway loft.