Vacation rentals with a kayak in Milford

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Popular amenities for Milford kayak rentals

House rentals with a kayak

Top guest favorite
The exterior of a two-story waterfront home is shown, featuring a modern design with blue siding. A spacious deck is visible above a landscaped area with carefully arranged plants and gravel, while a driveway leads to the front of the house, surrounded by greenery.
Home in Rocky Hill
4.96 out of 5 average rating, 25 reviews

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT

AdamRating, 5 stars2 days ago
Great location. Great space. Everything was in excellent condition. Our family had a wonderful time.
Guest favorite
An aerial view captures a spacious lakefront property surrounded by lush greenery. Trees frame the yard, which gently slopes toward the water. The exterior of the house is clad in light gray, with multiple windows reflecting the natural surroundings. A patio area is visible near the water's edge.
Home in Putnam Valley
4.96 out of 5 average rating, 82 reviews

Crystal Wave LakeHouse

IbrahimRating, 5 stars4 weeks ago
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.
Guest favorite
A serene lakeside view captures a vibrant sunset reflected on the calm water. The sky is filled with shades of orange and purple, framed by distant hills. A stone wall borders the foreground, leading into a pebbled area near the water's edge.
Home in East Hampton
4.88 out of 5 average rating, 26 reviews

Lakeside Paradise with Breathtaking Sunsets

MaileeRating, 5 stars1 week ago
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!!!
Top guest favorite
A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.
Home in North Fork
5 out of 5 average rating, 12 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

TimothyRating, 5 stars1 month ago
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!!
Top guest favorite
A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.
Home in Old Saybrook
4.97 out of 5 average rating, 122 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

SueRating, 5 stars1 month ago
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.
Top guest favorite
A bright and airy space features large windows that provide scenic views of the water. A cozy seating area with patterned cushions is positioned along the window ledge. A set of twin bunks is also visible in the room, enhancing the inviting atmosphere.
Home in Madison
5 out of 5 average rating, 55 reviews

Writer's Retreat & Explorer's Adventure!

KathrynRating, 5 stars1 week ago
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!
Guest favorite
A serene backyard is depicted, featuring a soft green lawn bordered by flourishing plants and flowers. Stone pathways meander gently through the garden, leading towards a view of the water. Trees provide shade, enhancing the natural, peaceful setting.
Home in North Fork
4.92 out of 5 average rating, 25 reviews

Coastal Cottage on the Water

MeghanRating, 5 stars1 week ago
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!
Guest favorite
The image captures an open door with a polished metal knocker, revealing a glimpse of an ornately patterned rug and a side table adorned with a lamp. The warm light envelops the space, contrasting with the dark door and inviting entryway.
Home in North Fork
4.9 out of 5 average rating, 30 reviews

4 Bedroom Beach Bungalow

JohnRating, 5 stars4 weeks ago
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

Guest favorite
A charming waterfront cottage is seen from the water, surrounded by lush trees. A spacious deck with a canopy extends outward, while two individuals enjoy the water on a paddleboard. The shoreline features a rocky edge and a grassy area leading up to the cottage.
Cottage in Branford
5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

BasilRating, 5 stars9 months ago
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.
Guest favorite
A dining area offers a wooden table surrounded by black chairs, with large windows overlooking the lake. Slate flooring complements the bright, airy space, creating a seamless connection to the outdoor views. Natural light fills the room, enhancing the serene ambiance.
Cottage in Putnam Valley
4.96 out of 5 average rating, 163 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

MichelleRating, 5 stars6 days ago
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!
Top guest favorite
Two wooden chairs are positioned on a grassy area overlooking the calm water. A fire pit sits in between the chairs, and a swing hangs from a nearby tree. In the background, a dock extends into the water, framed by trees.
Cottage in Shelter Island
4.97 out of 5 average rating, 108 reviews

Shelter Island Waterfront Getaway

CindyRating, 5 stars5 months ago
Great stay, Maureen is very communicative and super helpful. Beautiful views
Top guest favorite
A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.
Cottage in Shelter Island
4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Lisagitelson@Gmail.ComRating, 5 stars7 months ago
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.
Guest favorite
A backyard patio area is shown, featuring a seating arrangement of several chairs and a table. A fire pit is positioned on a stone surface, surrounded by grass and landscaping. The view overlooks the lake, with boats visible in the background and lush trees framing the scene.
Cottage in East Haddam
4.9 out of 5 average rating, 131 reviews

Direct Waterfront Cottage on Moodus Reservoir.

WendyRating, 5 stars1 week ago
Nice little spot with boats on the pond. Went there for my son’s Wesleyan graduation and could take family out on the kayaks.
Guest favorite
The exterior of the cottage is shown, featuring a sloped roof and grey shingles. A front porch is visible, with a flag displayed on one side. Lush green grass and landscaping surround the home, while trees provide a natural backdrop.
Cottage in Lebanon
4.87 out of 5 average rating, 150 reviews

Go Jump in the Lake!

KirstenRating, 5 stars1 month ago
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.
Guest favorite
Sunlight emerges over a tranquil lake, casting golden hues across the water. Tall trees frame the scene, with dense greenery surrounding a wooden deck. The sky displays a blend of soft blues and whites, creating a peaceful natural ambiance.
Cottage in Putnam Valley
4.89 out of 5 average rating, 270 reviews

Lakefront Cottage near Hudson Valley

BrianRating, 5 stars1 month ago
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.
Top guest favorite
Two kayaks are positioned near a red shed, featuring distinct colors of yellow, black, and green. The grassy area surrounding them is well-maintained, highlighting the inviting outdoor space of the cottage.
Cottage in Old Lyme
4.98 out of 5 average rating, 46 reviews

Cottage with Roger’s Lake Views

AngelaRating, 5 stars1 week ago
Nice and quite. Cabin like feel. Great place to get away from the hustle and bustle of life.

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 stars9 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!
Guest favorite
A solitary kayak gently glides across the calm waters of a lake surrounded by lush green hills and scattered islands. The serene sky features soft, fluffy clouds, reflecting a tranquil atmosphere perfect for a day of outdoor exploration.
Cabin in New Fairfield
4.96 out of 5 average rating, 328 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

Julissa & AlyssaRating, 5 stars1 week ago
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 🐾
Guest favorite
A charming yellow cottage is framed by green trees and a bright blue sky. The exterior features a spacious front porch with large windows and white railings, inviting natural light. Steps lead to the entrance, surrounded by well-kept grass and a few decorative plants.
Cabin in Bethlehem
4.9 out of 5 average rating, 30 reviews

Swim, fish, kayak & RELAX!

GeraldRating, 5 stars1 week ago
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.
Top guest favorite
The cabin is surrounded by lush greenery, with warm lights strung across the deck creating a cozy ambiance. Large windows reflect the evening glow, showcasing a welcoming entrance. The sky transitions from deep blue to vibrant orange, adding to the serene setting of the retreat.
Cabin in Bethlehem
4.95 out of 5 average rating, 78 reviews

Cabin by the lake I Private Beach I Paddle Board

OliviaRating, 5 stars1 month ago
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!
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 stars9 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...
Top guest favorite
A spacious outdoor area features a private dock along the lake, with multiple lounge chairs positioned for relaxation. Lush greenery surrounds the well-maintained yard, and a series of steps leads to the cabin. Soft lighting enhances the serene environment at dusk.
Cabin in East Haddam
5 out of 5 average rating, 18 reviews

Lakeshore Cabin with boat dock

IrenaRating, 5 stars2 weeks ago
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!
Superhost
A quaint cottage is situated amidst a lush yard, surrounded by trees and colorful foliage. A pathway leads to the front door, while a swing hangs from a nearby tree. Leaves cover the ground, complementing the natural setting.
Cabin in South Salem
5 out of 5 average rating, 4 reviews

Casa Luna Lake Cottage

DanielRating, 5 stars1 month 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
4.85 out of 5 average rating, 74 reviews

Candlewood Cabin - with Private Waterfront

CaroleRating, 5 stars2 weeks ago
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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