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

G$74,657 GYD 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.

Sep 16 – 23

G$113,946 GYD per night

Guest favorite

Home in Milford

4.95 out of 5 average rating, 43 reviews

Salty Kisses Beach Cottage Milford CT

Salty kisses cottage. The perfect getaway. Wake up & enjoy sunrise in front of this cozy house. Beach access across street. Public beach and Silver Sands Park end of road . Enjoy long walks on the boardwalk to Walnut Beach find the lazy lobster, ice cream parlor, fresh juice. Greek spot cafe. Silver Sands State Park has a brand new boardwalk and pavilion.. Scenic bike route. Bring your bikes. Enjoy shopping downtown,.seafood, music,farmers market. . Super Clean! Private yard w grill. Wifi

Jul 15 – 22

G$79,555 GYD 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!

Sep 5 – 12

G$108,204 GYD per night

Guest favorite

Home in Milford

5.0 out of 5 average rating, 71 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

G$58,258 GYD 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.

Nov 11 – 18

G$60,366 GYD per night

Guest favorite

Home in Milford

4.97 out of 5 average rating, 70 reviews

Connecticut Waterfront Beach House Retreat

Get away from the stress of daily life at this cozy waterfront beach house. Wake up to breathtaking sunrises, spectacular water views, and the sound of waves outside your window. Feel your body relax while your stress melts away as you relax on the beach, patio, or by a warm fire with a cocktail or a good book. Take a walk or run on the beautiful beach. Enjoy making memories with family, friends, and loved ones while counting stars under an expansive moonlit sky.

Aug 11 – 18

G$118,284 GYD per night

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 310 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.

Jan 30 – Feb 6

G$92,502 GYD 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!

Mar 18 – 25

G$89,315 GYD per night

Guest favorite

Home in Rocky Point

4.91 out of 5 average rating, 178 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.

Dec 3 – 10

G$33,041 GYD per night

Guest favorite

Cabin in New Fairfield

4.98 out of 5 average rating, 257 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

Sep 5 – 12

G$86,720 GYD per night

Superhost

Cottage in Milford

4.85 out of 5 average rating, 60 reviews

Cheerful 3 Bedroom Cottage with Fire Place

Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need while on vacation. Including, comfortable beds, beach strolls and a bright upgraded kitchen with all the amenities you will need. The 3 bedrooms will fit up to 8 people comfortably.

Dec 27 – Jan 3

G$72,285 GYD per night