Cottage vacation rentals in Jamesport

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Top-rated cottage rentals in Jamesport

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Guest favorite

Cottage in North Fork

4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Guest favorite

Cottage in Westhampton Beach

4.93 out of 5 average rating, 164 reviews

Cool Tiny Cottage Artist Loft!

He Loved All Things Sea & I Followed Suit. 38 Years Ago My Father Built This Very Special Artist Loft Cottage Retreat. This Tiny Home is One Of A Kind. Throughout The Years Guests & Family Have Come & Gone Creating Beautiful Memories. The Space Is Tranquil, Serene, Peaceful & Harmonious. It’s A Wonderful Romantic Space, Charming For Family Gatherings, or One For A Soul Heart In Transition. All Have Found Passion, Peace and Progress Here. The Cottage Boasts A Fully Fenced In Large Yard, Deck, Grill, Light & Airy Vaulted Ceiling In Living Room With A Chenille Slip Cover Queen Sleeper and Cool Lounger With Library Bookcase With Books And Stereo/CD/Cassette, Color TV & DVD. Staircase to Loft Full Bed & Cute Twin Bed Area. Very Clean & Decorated Adorably. Wifi. Linens & Kitchen equipped, Washer/Dryer. Dining Table for 4 W/Sliders to Deck. Outside Seating for 6 & A Gas Grill. Perfect Place for 2. Quiet At End Of St. 1.5 miles to Rogers Beach Dune Rd/Ocean. 1 Mile To Main Street Village. 15 min to North Fork Wineries & Farms. Agent owned.

Guest favorite

Cottage in Guilford

4.95 out of 5 average rating, 177 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Guest favorite

Cottage in Westbrook

4.89 out of 5 average rating, 151 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Top guest favorite

Cottage in North Fork

5 out of 5 average rating, 31 reviews

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

Top guest favorite

Cottage in Waterford

5 out of 5 average rating, 15 reviews

Game Room-Mins to Beach&Boardwalk-Walk to Marinas

The perfect cozy cottage with game room and 3 queen beds - enjoy everything the CT shore has to offer. Desirable location allows for walks along the river, down to the marina + restaurants, or over the bridge to the Niantic Boardwalk. Launch your boat or kayak across the street - driveway has space for your trailer! Relax after a beach day in the back yard - fully fenced with grill, picnic table + fire pit! Quick drives to Harkness Memorial, BI Ferry + Rocky Neck! ~20min to Mystic

Guest favorite

Cottage in Milford

4.95 out of 5 average rating, 314 reviews

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 131 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Top guest favorite

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Top guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 141 reviews

Coastal Cottage Private Studio

Beautiful coastal studio cottage located on the shoreline of CT. Your cottage is spacious and private with keyless entry and private dedicated parking. Originally an art studio, this recently renovated cottage is one mile to the beaches and local attractions. Our cottage is popular among Connecticut College, Coast Guard Alumni/parents and for anniversary celebrations! Enjoy...Now you can kick back and relax... you've found your home away from home! 🤩🏡 😊

Superhost

Cottage in Clinton

4.82 out of 5 average rating, 39 reviews

The Beach Nest-Lux Cottage Steps to the Beach

Come enjoy the cutest cottage on Shore Rd. Newly renovated. Just steps to the beach and minutes away from town and all of the CT shoreline attractions. This newly renovated cottage has all the modern amenities of today and all the old charm of yesterday. The cottage features water views, a fully equipped kitchen, washer/dryer, and dishwasher. The cottage sleeps up to 6 (1 queen,1 bunkbed, and 1 sleeper sofa)and has parking for 2 cars.

Superhost

Cottage in Sag Harbor

4.87 out of 5 average rating, 102 reviews

Secluded Hamptons Cottage

This cottage has high ceilings, is bright and airy, has a wrap around deck with a great overhang for hanging out in the shade or sun. You can not see a neighbor. It has been described as “an adult tree house.” Just a fun and relaxing place to be. It is on over an acre of rustic property. Perfect for watching wildlife.

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What guests are saying

Renovated beach cottage a block from private beach

4.88 out of 5 average rating, 40 reviews8 months ago

April’s cozy beach cottage was perfect for my elderly parents. Everything was spotless, and although tiny, the kitchen was fully stocked with a large refrigerator and full stove, microwave etc. both the bed and the sofa were v comfortable and most importantly, April made sure there was AC in every room, even the cute porch. There’s an outdoor shower which is super convenient. You can easily walk to the beach, go to the arcade, kokomos, a crepes place and the carousel and gift shop. Very peaceful retreat. Must also mention how cheerfully it’s decorated and how spotlessly clean! Just lovely.

Cottage in Old Lyme

What guests are saying

Hop Skip and a Jump to the Beach

4.97 out of 5 average rating, 35 reviews8 months ago

Our first ever stay at 'Hop Skip and Jump' really met all of our expectations and needs for the week of 8/10-8/17/24! I have never in my 70+ years of spending a summer week in Old Lyme been so enveloped with 5 star luxury while at the Beach! I would recommend this rental to any small family or a group of girlfriends! Hop

Cottage in Old Lyme

What guests are saying

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

4.95 out of 5 average rating, 99 reviews3 weeks ago

Very comfortable. See through shades in bedroom and living area needed to be not so see through. Also could have used a dresser in the bedroom. Hard to get in and out of the driveway. We had a pickup. Other than that we thoroughly enjoyed our stay.

Cottage in Milford

What guests are saying

Remodeled Cottage Private Old Kelsey Point Beach

4.52 out of 5 average rating, 21 reviews8 months ago

Cheryl's place was adorable! I felt right at home in the cosy open concept living space. My mom crashed the weekend portion of the trip which was nice. My cat Mushu had a wonderful time and we even went outside. The beach was about a four minute walk for me, and a breathtaking view as you approach. Cheryl had everything necessary and mentioned. Next time I'll be sure to bring coffee filters and sugar. There were unexpected amenities too like paper towels and trash bags, and candles. There were also tons of spare toiletries like shaving cream and shampoo and conditioner and body wash. Thanks again!

Cottage in Westbrook

What guests are saying

Adorable Cottage

4.95 out of 5 average rating, 41 reviews3 months ago

This magical cottage is a little slice of paradise. It’s so incredibly cute and cozy but beyond that, Erin Leigh has put in so many thoughtful touches- we wanted for nothing. It’s clean, it’s beautiful, it’s comfortable…truly one of the best places I’ve ever stayed in. Her hospitality was top notch. I felt so spoiled and so sad to leave.

Cottage in North Fork

What guests are saying

Charming historic cottage in Setauket, NY

5 out of 5 average rating, 84 reviews2 months ago

I booked this cottage for my family quickly and only a day or two in advance, barely looking at the listing beyond location and sleeping arrangements. When we arrived, we were all pleasantly surprised at how comfortable and lovely this little home was. I have never encountered such a thoughtfully designed rental. I was recovering from a surgery, had two weary young children, and we were in town for an unexpected funeral. From the games to the beds to the toiletries, every aspect of this cottage soothes and welcomes. Our stay made a difficult time a little easier, and I am very appreciative to Lise for creating such a hospitable and lovely cottage and sharing it with others.

Cottage in Setauket- East Setauket

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