Vacation rentals with a kayak in Milford

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Top-rated kayak rentals in Milford

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Guest favorite
A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.
Home in Milford
4.98 out of 5 average rating, 134 reviews

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

Guest favorite
A lakeside patio is depicted, featuring several metal chairs arranged around a firepit. Two swinging chairs hang from a pergola, while a dock with a boat and kayak is visible on the water. A vibrant American flag flutters in the background.
Guest suite in Newtown
4.92 out of 5 average rating, 106 reviews

waterfront on Lake Zoar[ SUITE]

Enjoy your private patio overlooking the lake, Or just walk 12 steps to water Edge and visit the cozy lower level and enjoy the swings . Use our kayaks, and don’t forget to bring your fishing pole, go swimming ,or just sit in the sun with a book and listen to the waterfall and you are welcome to sit by the firepit Optional boat dock space, parking Hosts live upstairs Two miles to quaint Sandy Hook center with grocery and restaurants All quests must be register Ninety minutes to Boston/nyc

Guest favorite
A dining area features a wooden table surrounded by dark chairs, set with blue and white plates. Large windows allow natural light and provide an expansive view of the lake, where boats can be seen in the distance.
Cottage in Middlefield
4.97 out of 5 average rating, 109 reviews

Anchors' Away-

Anchors Away! Is the perfect setting for a quick get away! Or a prolonged vacation! Where reading, chilling, fishing, boating are not just words--Its a state of mind!! If you were any closer to the lake, you would feel as if you were on a houseboat... Every amenity is here for you to enjoy. Convenient to Interstate 91, Merrit Parkway, RT. 9.Recently gut renovated you will find the luxury of a hotel, yet quiet enjoyment. The property has two full bedrooms-one full bath-large great room!

Guest favorite
A bright living area features large glass doors that open to a beautiful view of the ocean. Comfortable seating includes a sectional sofa and accent chairs, with a modern TV and light wood flooring adding to the ambiance. An umbrella provides shade for outdoor seating on the deck.
Home in Milford
4.94 out of 5 average rating, 48 reviews

Charming 3 bedroom Beach Front Cottage

there is still time to enjoy the fall, the solitude of the beach 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.

Top guest favorite
An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.
Home in Milford
5 out of 5 average rating, 116 reviews

Steps2Beach, Fish Pond, Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Top guest favorite
A bright dining area is highlighted by large windows that allow natural light to fill the space. A rustic wooden table is adorned with a floral centerpiece consisting of small vases, each housing a single flower. The room features light-colored walls and attractive white chairs.
Cottage in Fairfield Beach
4.98 out of 5 average rating, 126 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Guest favorite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 416 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, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Guest favorite
A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.
Home in Milford
4.96 out of 5 average rating, 119 reviews

Oceanfront Retreat 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
A wooden dock extends towards a serene lake, surrounded by green hills. A kayak rests on the shore, inviting exploration. The scene is framed by the branches of a tree, adding a touch of nature to the peaceful waterfront view.
Home in Danbury
4.88 out of 5 average rating, 163 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.

Top guest favorite
A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.
Cottage in Guilford
4.94 out of 5 average rating, 281 reviews

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.

Guest favorite
The outdoor space features a hot tub surrounded by natural greenery, providing a serene environment. A cozy cabin with inviting lighting is visible in the background, while torches are placed nearby to enhance the ambiance. Gravel pathways lead to both the hot tub and cabin entrance.
Cabin in New Fairfield
4.96 out of 5 average rating, 357 reviews

Little Lake Cabin | CT Getaway w/ Hot Tub & Kayaks

Named one of the Best Airbnbs in Connecticut by Business Insider, The Little Lake Cabin is a cozy Connecticut lake cabin perfect for relaxing, hiking, and reconnecting with nature. Just steps from Candlewood Lake and Squantz Pond State Park, enjoy kayaking, evenings by the fire pit, or a soak in the hot tub under the stars. Your peaceful New England getaway awaits, ideal for couples, friends, and nature lovers alike.

Guest favorite
A modern cottage is set amidst lush greenery, featuring a spacious rear deck and a lower patio area with two lounge chairs. The second story includes a covered deck with an awning, while large windows invite natural light into the interior.
Home in North Fork
4.94 out of 5 average rating, 105 reviews

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 Milford kayak rentals

When is the best time to visit Milford?

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Avg. priceG$55,364 GYDG$53,275 GYDG$62,676 GYDG$65,810 GYDG$67,481 GYDG$78,136 GYDG$87,329 GYDG$73,331 GYDG$71,451 GYDG$62,676 GYDG$62,676 GYDG$66,437 GYD
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Quick stats about vacation rentals with a kayak in Milford

  • Total vacation rentals

    Explore 30 vacation rentals in Milford

  • Nightly prices starting at

    Milford vacation rentals start at G$20,892 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,470 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Milford vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Milford rentals

  • 4.9 Average rating

    Milford stays are highly rated by guests—averaging 4.9 out of 5!