
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

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT
Great location. Great space. Everything was in excellent condition. Our family had a wonderful time.

Crystal Wave LakeHouse
Great stay at Carl's place. The location is wonderful and the house is stacked with amenities. We were a party of 7 and everyone was comfortable during their stay. Only issue I will highlight is that the living area and one of the rooms need blinds/curtains for privacy reasons as well as sunlight waking you up in the morning. Overall great stay and wont hesitate coming here again.

Lakeside Paradise with Breathtaking Sunsets
Amazing house! We rented the lake house and guest house to spend time with family and friends during our son’s graduation at Wesleyan. I stayed in the guest house. It was so cozy with great modern amenities. It was the perfect place to relax and close to the school. Being close the lake was a definite plus. I highly recommend!!!

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

Year Round Beach House in Old Saybrook, CT.- Pets
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.

Writer's Retreat & Explorer's Adventure!
River House was beautiful and the location is amazing! The house is clean and tastefully decorated. Alison was very friendly and responsive and the house book was very helpful. We really enjoyed our stay and look forward to booking again!

Coastal Cottage on the Water
Loved our girls’ getaway on the North Fork! Mae’s house is the perfect spot with a quick walk to the beach and gorgeous views right from her backyard - even close drives to beautiful Southold, Mattituck, and Greenport. I will absolutely stay again!

4 Bedroom Beach Bungalow
Jennifer‘s place was absolutely amazing. Very cozy and warm and made you feel like you were basically removed from the world a fantastic place to just go and relax, even though there’s plenty of things to do in the area, including many great restaurants and wineries of course. The fire pit was the bonus. We had a fire every night we were there very simple to buy wood along the roadways. This place is definitely a top recommendation and we will definitely be back thank you Jennifer.
Cottage rentals with a kayak

Beachfront Cottage Serene Private Beach, Kayaks
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.

Private Lake House 1 Hour to NYC & Near Westpoint
We had a wonderful stay at Benjamin's lake house. The views are incredible, and the house comes with life vests and a peddle boat, 2 kayaks and a SUP board so you can easily take advantage of the lake! The house is one of the most well stocked houses I've ever stayed at, and is very family friendly - there are lots of toys for kids, and has a pack and play, sleeping mat, and high chair, and kids utensils. Benjamin's communication was extremely quick and he was always very helpful and responsive. We'd definitely stay here again!

Shelter Island Waterfront Getaway
Great stay, Maureen is very communicative and super helpful. Beautiful views

3 Bedroom Cottage Gem
This is the absolute perfect home for a get away. Everything you need and more is provided. The home is gorgeous, well decorated, and extremely clean. It is even better than the pictures. It feels like a real home, with luxury and artistic touches, not a generically decorated place. Location is perfect, close to it all and still very private. Christopher is an excellent host, responsive, helpful, and gives you your privacy. I can't recommend staying here enough.

Direct Waterfront Cottage on Moodus Reservoir.
Nice little spot with boats on the pond. Went there for my son’s Wesleyan graduation and could take family out on the kayaks.

Go Jump in the Lake!
Easy to find and access. Clean and neat. Looked just like the pictures! It was what I looking for when booking! Yeah!! Host responsive and friendly.

Lakefront Cottage near Hudson Valley
Stayed for a long weekend with my wife and two dogs. Cottage was comfortable and clean with an amazing view of the lake with a nice patio and access to the dock which we enjoyed. Also great location just a bit over an hour from the city but within a 15 minute drive to many great hikes and close to many great food options. Tony was also very responsive and helpful with recommendarions. Highly recommend.

Cottage with Roger’s Lake Views
Nice and quite. Cabin like feel. Great place to get away from the hustle and bustle of life.
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!

The Little Lake Cabin— hot tub, fire pit, & kayaks
I would like to start off by saying this cabin is so beautiful. It’s well decorated and creates this cozy homey appeal, making it feel like a home away from home for my partner and fur babies. The home has great privacy - enjoyed the hot tub & made s’mores (which was provided by the host). There’s a nice hike at Squantz Pond State Park you can do with nice views. Host is very attentive. Checks-in and has great response time. Also, provides a Welcome Book that provides nearby places you could hike, restaurants you could eat at, etc. Really enjoyed our time here. Hope to return in the future. - A, J & fur babies 🐾

Swim, fish, kayak & RELAX!
We stayed for a graduation near by, it was perfect for we were looking for. I wish the weather would have been a bit warmer to enjoy the water.

Cabin by the lake I Private Beach I Paddle Board
A few of us stayed at Mariana's for a girl's weekend to go to local events- and had a wonderful stay! The apartment was really aesthetic and perfect for a girl's trip, and we loved cooking in the kitchen as she had every appliance we needed, and loved the fireplace. Everything was cozy, well described, and had everything we could have needed! Mariana was friendly and helpful leading up to and during our stay. We'd recommend this for anyone wanting a cozy getaway!

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...

Lakeshore Cabin with boat dock
We spent a long weekend at Dennis’ place and it was nothing short of amazing. Our aim was to relax and enjoy the lake, and we did just that. The house was exactly as described, matched and exceeded our expectations; furnished and the kitchen had everything we needed and more. If we’re back in CT, we won’t hesitate to book the house again! Thanks for being wonderful hosts!

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
We really enjoyed our stay. We needed a place near Norwalk and Darien for post-op recovery, and chose this place for the peaceful vibe. I was able to run errands, hike, and even go into the nearby towns to visit Planet Fitness, while my son relaxed and recovered in the cabin. The kitchen had nearly everything we needed for me to cook for a week (there was no skillet, but plenty of pots and pans, knives & cutting boards, utensils—even a pizza cutter). The cabin has a euro-style washer/dryer combo, which has handy if slower than I'm used to. There's a helpful note that says washing/drying takes 6 hours so plan ahead, but I googled the unit and found some handy workarounds. The cabin wasn't supplied with coffee, laundry detergent, dishwashing detergent, or extra garbage bags. Those were easy enough for me to grab when I went grocery shopping, and Scott was very responsive when I let him know. Overall this was a really great experience!
Quick stats about vacation rentals with a kayak in Milford
Total rentals
30 properties
Nightly prices starting at
R$508 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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