
Vacation rentals with a kayak in Middlesex County
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Middlesex County
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

HideAway UConn Coventry RockFarm BnB Breakfast A+
Welcome to “The Hide Away” on Rock Farm with Superhosts Jon & Jeri. A private, family-friendly 1000+ sq ft wooded retreat featuring two bedrooms, 500 Mbps WiFi, Roku TV, private deck, full kitchen, laundry, and DIY breakfast. Just 15 minutes to UConn and 2 minutes to Bolton Lakes for fishing and hiking. See our VIP Guest Book for local favorites. Clean, cozy, no-shoe secluded BnB — 5⭐️ guest favorite. Ask about “The GetAway” too! It’s our King Studio Suite, a private space, perfect for couples.

Anchors' Away-
Welcome to your private lakefront sanctuary. Have the chance to make memories whether it is by fishing on either of the two docks? or the chance to kayak to explore the lake. Completely renovated with comfort and style in mind, this waterfront getaway offers panoramic lake views and direct water access. Start your mornings with coffee on one of the two private docks watching the sunrise. Unwind each evening on the patio all decked out with restful seating and a chance to watch the fireflys.

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Classic Lakehouse~Fire Pit_Canoes_Kayaks & Sunsets
Private lakefront home on Lake Pocotopaug with a fishing dock, kayaks, fire pit, and spectacular sunset views — perfect for family & friend getaways. Welcome to Lakeside Ferns, where you’ll enjoy direct waterfront access and private dock for swimming, fishing, kayaking, canoeing, and boating. Grill dinner, relax in the hammock by the water, and gather around the outdoor fire pit for s’mores under the stars. End each day with breathtaking sunsets over the lake — beautiful in every season.

Beautiful lakefront retreat just 15 mins to casino
Beautiful waterfront home with unobstructed views of Oxoboxo Lake! Quiet area yet just 30 minutes to Mystic. Upper level has 2 cozy bedrooms – one with a queen bed and one with 2 twin beds, a spacious living area with direct lake views, and a full bathroom. Lower level has a second mini kitchen with fridge, sink, microwave and table, large living room, bathroom, and doors leading directly onto the lakeside patio. Lower level has a twin size bed in living area for extra sleeping space.

Cozy Cottage |Quintessential CT | Pet Friendly
Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Cozy cottage 5 minutes from UConn
Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

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.

Go Jump in the Lake!
Our recently renovated lake house is situated on 1.5 acres just 250 steps to the Cove Road boat launch on beautiful Amston Lake. The lake is a pristine 188-acre retreat located in Lebanon and Hebron, CT. Swimming, kayaking, canoeing, paddle boarding, fishing, and sunbathing are all activities you can enjoy. There are no motor boats allowed so you can enjoy all of those activities in a peaceful environment. Two beaches are located 1/2 or 1 mile away with ample parking at both

Oceanfront Beach House w/ Private 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.

The Cottage at Indian Cove
A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Walk to Breakwater Beach in Heart of Wine Country
Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.
Popular amenities for Middlesex County kayak rentals
House rentals with a kayak

Waterfront Hot Tub Retreat Near Foxwoods & Casinos

Cozy Waterfront Home w/ Hot Tub Connecticut River

Coastal New England Waterfront Home-The Reed House

Charming Riverview Home • Firepit • Train & I-95

Year Round Beach House in Old Saybrook, CT.- Pets

Thames River Cottage · Near Casinos + USCGA

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

5 Star Branford Cozy Cottage Steps from the Beach
Cottage rentals with a kayak

Cozy, bohemian, lake front cabin in the woods

Salty Kisses Beach Cottage Milford CT

Little Gem Waterfront beach home/ cottage

Vintage Bolton Lake

Cheerful 3 Bedroom Cottage with Fire Place

Stunning waterfront modern farmhouse with dock.

Cottage at the Marina

The Bay Breeze
Cabin rentals with a kayak

Casa Lago

Riverfront Antique Cabin in the Heart of Madison

Swim, fish, kayak & RELAX!

Private Beach, Paddle Board, Swim

Lakefront - King - W&D - Fire Pit - Kayaks - Stand Up Paddleboards

Waterfront Cabin: Love Lake Life

Beautiful lakeside summer home

Lakeshore Cabin with boat dock
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Rentals with a washer and dryer Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with an EV charger Middlesex County
- Beachfront rentals Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with lake access Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with breakfast Middlesex County
- Guesthouse rentals Middlesex County
- House rentals Middlesex County
- Rentals with beach access Middlesex County
- Rentals with pools Middlesex County
- Apartment rentals Middlesex County
- Rentals with a patio Middlesex County
- Private suite rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with a fire pit Middlesex County
- Rentals with a hot tub Middlesex County
- Family-friendly rentals Middlesex County
- Bed and breakfasts Middlesex County
- Rentals with a kayak Connecticut
- Rentals with a kayak United States
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Six Flags New England
- Fairfield Beach
- Charlestown Beach
- Southampton Beach
- Ocean Beach Park
- East Matunuck State Beach
- Mohegan Sun
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Mystic Seaport Museum
- Sleeping Giant State Park
- Mount Southington Ski Area
- Long Island Aquarium
- Burlingame State Park
- Ski Sundown
- Orient Beach State Park
- Mystic Aquarium
- Ocean Beach
- Wölffer Estate Vineyard
- University of Connecticut




