Holiday rentals with a kayak in Middlesex County

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.

Beautiful lakefront home, 4bed 2.5ba

Fully renovated, on 80ft of lake front. Perfect for summer water activities, stunning fall foliage and often ice skating in the winter! East-facing with stunning sunrises. Very well equipped kitchen, cosy sitting room with wood-burning stove, dining room for 8, and powder room. Large porch faces the lake, with a sitting area, and dining table for 8. Ground floor king-size master & bathroom, with stunning lake views. Upstairs, 3 queen bedrooms, all with lake views and ample closet space.

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.

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.

Vintage Bolton Lake

Now booking for 2026! Enjoy vintage charm and the calming lake waters. Vintage is nestled on the shores of picturesque Middle Bolton Lake. Relax, unplug, and savor the good life of times past. The cottage has been tastefully updated and outfitted with period furnishings to allow for vacationing in comfort and style. As our guest, you will enjoy full use of the cottage, WiFi, property, propane grill, smokeless firepit, kayaks and much more. Come enjoy vintage lakefront lifestyle.

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

The Blue Heron at Amston Lake

3 BEDROOM Quiet Cottage: ~3 minute walk to the Main Beach at private Amston Lake. ~ Fully stocked open floor plan kitchen. Dining table seats 4 with additional seating on covered patio accessible by sliding door. ~Gas grill ~Large, private backyard with fire pit and hammock. ~Canoe and kayak available ~Adult bicycles (2) available upon request. ~Ping pong table, dart board in basement. ~ Close to Airline Trails, vineyards, breweries, casinos, and parks.

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.

Direct Waterfront Cottage on Moodus Reservoir.

Relax with the whole family at this peaceful place to stay with direct access to the lower Moodus Reservoir. The backyard leads out to the lake with a small beach area (fits approximately two lawn chairs). Sit on the patio by the fire pit and enjoy the view or grab a kayak, pedal boat, or paddleboard and enjoy your time directly on the lake.