
Vacation rentals with a kayak in Milford
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Top-rated kayak rentals in Milford
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House rentals with a kayak

Spacious Lake Home for Peace and Relaxation
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 !

Once a Pond - time and stress slow down.
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.

The Katalpa House -by the beach
Amazing place, super accommodating, and so understanding. Experience was absolutely amazing.

Beach Home & Garden Paradise
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.

Stay at Old Dorset Farm & create lifelong memories
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.

Waterfront with private dock & bocce court
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. ❤️

Private Beach access along the Wine Trail
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!

Beachfront paradise- come, stay, relax!
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

Longview Lakehouse - 5 min walk to private beach
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.

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

Pumpkins & Sunflowers! Cozy Cottage in the Fall!
Had a nice stay here with a group of people attending a wedding a short drive away.

Salty Kisses Cottage Relax
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!

The Cottage at Indian Cove
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.

Charming Fairfield Beach 3BR Cottage By The Sea
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.

Cottage at the Marina
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.

Your own Thimble Islands private cottage!
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

Lakefront cabin with private dock on stunning cove
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!

Beautiful lakeside summer home
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...

Casa Luna Lake Cottage
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.

Candlewood Cabin - with Private Waterfront
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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- Beach
- Yale University
- Gilgo Beach
- Bronx Zoo
- Dunewood
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Robert Moses State Park
- Rye Town Beach
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Bethpage State Park
- Marvin Beach
- Jennings Beach
- Seaside Beach
- Robert Moses State Park Field 2
- Connetquot River State Park Preserve
- Rockland Lake State Park
- Long Island Aquarium