Vacation rentals with a kayak in Milford

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Top-rated kayak rentals in Milford

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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

R6,619 ZAR 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

R9,548 ZAR per night

Guest favorite

Apartment in Branford

4.89 out of 5 average rating, 9 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.

Jan 14 – 21

R1,765 ZAR per night

Guest favorite

Home in Milford

4.98 out of 5 average rating, 82 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.

Nov 9 – 16

R8,518 ZAR per night

Guest favorite

Home in Milford

4.97 out of 5 average rating, 34 reviews

Beachfront paradise- come, stay, relax!

Looking for an island-feel getaway? You've arrived! Welcome to La Spiaggia. Come enjoy this 4 bedroom, 2 bath home and wake up to the sound of waves crashing on your private beach. Have a cup of coffee watching the beautiful sunrise, work from home on the oversized front porch, and enjoy the evening with beautiful lighting and sunset views. Take a stroll along the ocean to Bay View Beach, or simply relax and take in the expansive oceanfront views. Soak up the summer sun at La Spiaggia!

Nov 28 – Dec 5

R6,996 ZAR per night

Guest favorite

Home in Milford

5.0 out of 5 average rating, 73 reviews

Steps2Beach,Fenced GardenOasis, FishPond & kayaks!

⛵️Welcome to our luxurious gourmet home, nestled in the vibrant Art District. Experience culinary excellence in our fully equipped kitchen, surrounded by plush decor blending New Orleans charm with New England elegance. Step outside to our private oasis, complete with a vibrant garden and enchanting fish pond. Just steps from beaches, boardwalks, and global cuisine. Minutes from the Tyde wedding venue, downtown's culinary delights, and concert arenas. Your dream getaway awaits!

Sep 4 – 11

R5,210 ZAR per night

Guest favorite

Home in Milford

5.0 out of 5 average rating, 22 reviews

Lux cozy 2br/1ba Milford bungalow-walk to beach!

Beautifully updated bungalow 3 minute walk to beach. Features two decks for views & enjoyment of Silver Sands State Park. Back deck has teak dining table & grill for dinners, drinks, birdwatching, stargazing. House has outdoor shower, two double kayaks, stand up paddle board, paddles, beach chairs/towels, umbrellas, cooler, wagon. Spacious living room has tons of natural light. Bedrooms are cozy each with a full bed; primary opens to back deck. 5 min drive to downtown Milford.

Mar 23 – 30

R5,352 ZAR 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

R8,195 ZAR 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

R9,776 ZAR 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

R7,395 ZAR per night

Guest favorite

Home in Rocky Point

4.91 out of 5 average rating, 179 reviews

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Apr 8 – 15

R3,635 ZAR 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

R5,025 ZAR per night