Vacation rentals with a kayak in Milford

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Popular amenities for Milford kayak rentals

House rentals with a kayak

Superhost
Home in South Salem
4.85 out of 5 average rating, 33 reviews

Spacious Lake Home for Peace and Relaxation

RachelRating, 5 stars2 months ago
This is our second time renting this beautiful lakeside home and it was absolutely perfect for our girl's weekend. The kitchen was a dream, with all of the appliances and amenities you could need and plenty of room for everyone. The living room had so much seating and the fireplace made everything that much more cozy. All of the bedrooms had very comfortable beds with the best sheets and comforters. I think everyone was impressed with how well they slept. The owner was super easy to communicate with throughout our stay. We can't speak highly enough about this rental. Thank you !
Guest favorite
The living area features two comfortable, light-colored chairs positioned beside a small table. A large bay window allows ample natural light to fill the space, offering views of colorful foliage outside. Soft curtains frame the window, enhancing a welcoming environment.
Home in Fairfield
4.95 out of 5 average rating, 21 reviews

Once a Pond - time and stress slow down.

LindaRating, 5 stars3 weeks ago
This was a beautiful home to stay at for our visit to Fairfield University. It was peaceful location near the school. The house itself was gorgeous with everything we needed for our stay. Thank you.
Superhost
Home in Rocky Point
4.88 out of 5 average rating, 233 reviews

The Katalpa House -by the beach

JessicaRating, 5 stars1 month ago
Amazing place, super accommodating, and so understanding. Experience was absolutely amazing.
Guest favorite
A sandy beach area is depicted, featuring a simple wooden bench and a pink chair facing the calm waters of Long Island Sound. The shoreline is complemented by patches of green grass and distant boats can be seen on the horizon.
Home in Madison
5 out of 5 average rating, 16 reviews

Beach Home & Garden Paradise

NicoleRating, 5 stars3 weeks ago
We had a wonderful stay in Brian's charming home. The house is even more luxurious than in the photos--everything is first-class from the beds and linens; to the spacious kitchen with every new appliance you could need; to the comfy living room area with huge flat-screen TV. We had more than enough room for our family of four and our kids loved how close the private beach was, literally out the door. They kayaked and enjoyed walks on the beach. The area is in a very quiet, private neighborhood with close access to the shops and restaurants on Madison's main street. A perfect retreat any time of year, we hope to come back soon.
Top guest favorite
Home in Brookfield
4.98 out of 5 average rating, 144 reviews

Stay at Old Dorset Farm & create lifelong memories

MichaelRating, 5 stars6 days ago
This is our 2nd time staying at Ninka’s home. We had another great experience. Ninka provides everything you need for a great stay and is very accommodating. Highly recommend. 5 star experience again.
Guest favorite
Home in North Fork
5 out of 5 average rating, 17 reviews

Waterfront with private dock & bocce court

AlisonRating, 5 stars5 months ago
We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️
Guest favorite
A wooden walkway leads down to a calm beach, with gentle waves lapping at the shore. The water reflects a clear sky and distant land. A floating object is seen in the water, enhancing the serene coastal scene.
Home in North Fork
4.92 out of 5 average rating, 12 reviews

Private Beach access along the Wine Trail

RaeganRating, 5 stars1 month ago
I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!
Guest favorite
A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Cottage rentals with a kayak

Guest favorite
Cottage in Brookfield
4.91 out of 5 average rating, 34 reviews

Longview Lakehouse - 5 min walk to private beach

ChelseaRating, 5 stars3 months ago
Christienne was very responsive and helpful, the house was just as described and the location was so peaceful and quiet. Unfortunately I had to shorten my stay but I would absolutely be back if the opportunity presents itself.
Guest favorite
Cottage in North Fork
5 out of 5 average rating, 13 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

ChristinaRating, 5 stars1 week ago
Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!
Guest favorite
A sandy beach stretches along the shoreline, meeting calm blue waters under a clear sky. A wooden staircase leads down to the beach, surrounded by sparse vegetation and rocky areas. Soft clouds drift above, contributing to a serene coastal scene.
Cottage in North Fork
4.89 out of 5 average rating, 28 reviews

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

DanRating, 5 stars8 months ago
Had a nice stay here with a group of people attending a wedding a short drive away.
Guest favorite
The view from the front of a blue kayak showcases calm water reflecting a vast sky filled with gray clouds. Marsh grasses line the shoreline, with a few distant birds visible. The scene conveys a sense of tranquility in a natural setting.
Cottage in Milford
5 out of 5 average rating, 8 reviews

Salty Kisses Cottage Relax

KristinRating, 5 stars8 months ago
Our stay was perfect! The home was so clean and Denise even left us a baby gate for our 1 year old. Denise was very responsive and provided great recommendations of places to eat and things to do. There is a private beach across the street but we walked about .25 miles down the street to the Silver Sands State Park beach so that our 1 year old could play in more shallow water before high tide. We would highly recommend and will be back!
Top guest favorite
An aerial view captures the cottage's proximity to the beach, with sandy shores and gentle waves visible. The surrounding area features a blend of trees and homes, enhancing the scenic coastal environment.
Cottage in Guilford
4.94 out of 5 average rating, 262 reviews

The Cottage at Indian Cove

NicoleRating, 5 stars6 days ago
I thoroughly enjoyed my stay at this peaceful cottage. I enjoyed sipping my coffee looking at the view of the cove from the deck and the bird watching from the screen porch was a delight. The bed was comfortable and Gail stocked the kitchen with drinks and snacks! Gail's house is next door but the layout of the deck and screen porch offers great privacy. A perfect place to get away from it all and relax in nature.
Top guest favorite
A bright sunroom features a round table surrounded by two white metal chairs with blue cushions. Large windows allow natural light to fill the space, showcasing a coastal view. Straw hats are hung on the walls, adding a touch of seaside charm.
Cottage in Fairfield
4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

BriannaRating, 5 stars8 months ago
We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.
Top guest favorite
A private deck offers a view of the Indian River, featuring a circular glass-top table surrounded by four black wicker chairs. A red grill is positioned nearby, and the wood-like flooring extends across the outdoor space, with a railing providing safety and privacy.
Cottage in Clinton
4.97 out of 5 average rating, 30 reviews

Cottage at the Marina

CarolRating, 5 stars6 months ago
My stay at Chris and Ann’s listing was the perfect last stop on my stay in CT……beautiful, welcoming accommodations enhanced by the natural, peaceful, setting of the salt marsh and wildlife. It’s absolutely a favorite place the next time I’m visiting CT.
Guest favorite
Aerial view of a tranquil waterfront landscape featuring numerous small islands and rocky shorelines. The serene blue waters reflect sunlight, and a few scattered trees dot the land, enhancing the natural beauty of the coastal environment.
Cottage in Guilford
4.86 out of 5 average rating, 37 reviews

Your own Thimble Islands private cottage!

LilianRating, 5 stars6 days ago
We had an amazing stay with Sean and Jenny. The property is perfect for a peaceful getaway from the stresses of daily life- unique location, impeccable views, spotless and well furnished house, we were able to unplug and enjoy some nice quality time. Sean is a gracious host, offered lots of local recommendations as well as details of the house that were very helpful. Was responsive for questions and easy to communicate with. Hope to be back one day!

Cabin rentals with a kayak

Top guest favorite
A spacious wooden dock extends over calm lake waters, with a bright yellow kayak and paddles resting on its surface. Lush green hills are visible in the background, reflecting the serene environment.
Cabin in New Milford
5 out of 5 average rating, 8 reviews

Lakefront cabin with private dock on stunning cove

AlekseyRating, 5 stars7 months ago
We stayed here for 7 days with 2 small kids (2 and 4 years old) and wow was it amazing. The home is spacious and has everything we needed inside and outside the house. I could not have asked for anything else from the home and the dock was just so awesome to have, even caught 10+ fish right off the side. We rented a boat for a day from a marina and were able to come in and out of the backyard/house with no problems. I wish we could stay here for a whole month, but have to go back to real life!
The exterior of a stone cottage is surrounded by lush greenery, with a prominent stone chimney rising from the roof. A gravel pathway leads up to the entrance, framed by shrubs and small trees. The setting offers a natural feel, nestled among the trees.
Cabin in Stratford
4.81 out of 5 average rating, 44 reviews

Beautiful lakeside summer home

SondraRating, 5 stars8 months ago
We had a lovely 5-day stay at the cabin on the lake! It was just what we needed. When the weather was nice, we hung out on the dock - there was a hammock to relax in, chairs in the shed, boats to explore with (I went out in a kayak a few times). Lake was peaceful and pretty. The cabin itself was quirky and nice. Yes, hot inside during the days, but with the fully surrounding screened in porch, there was no need to stay inside! Even when it rained, we could be "outside" without being in the elements. The kitchen was well stocked, coffee at the ready, there were plenty of towels and sheets and bed (though we only needed one!), shampoo/ conditioner in the shower, wood ready for the fireplace, board games and more. Honestly, it had everything you'd want for a little getaway. The spot felt secluded while only 5 minutes away from a supermarket. [Okay, you could hear Rte 8 traffic a bit, but it served as calming white noise!] I'd definitely return again...
Superhost
A serene lake view is captured from a wooden dock, featuring two striped lounge chairs. A covered canoe rests on the side, while the calm water reflects a clear sky and autumn trees lining the shore in vibrant colors.
Cabin in South Salem
5 out of 5 average rating, 4 reviews

Casa Luna Lake Cottage

DanielRating, 5 stars2 weeks ago
The place was perfect for what we were looking for in a quiet weekend to explore the area. Joann was quick and responsive and went out of her way to make us welcome.
Superhost
Cabin in New Fairfield
4.84 out of 5 average rating, 70 reviews

Candlewood Cabin - with Private Waterfront

FrancinalvaRating, 5 stars1 week ago
Everything was perfect, I fell in love with the house, incredible view, wonderful place. I even felt like living there. The experience was worth it.

Quick stats about vacation rentals with a kayak in Milford

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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