Cottage vacation rentals in Sag Harbor

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Top-rated cottage rentals in Sag Harbor

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Guest favorite

Cottage in Riverhead

4.97 out of 5 average rating, 129 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, 147 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 Riverhead

4.86 out of 5 average rating, 134 reviews

Affordable Wine Country Cozy Cottage

Cozy cottage for relaxation in the beautiful, wooded, secluded historic community in Jamesport, on the North Fork just minutes from the Hamptons, wineries, bay beaches, antique shops, farms, bicycling and shopping. A walkable vacation with 6 wineries, 6 outstanding restaurants and bay beaches. Hampton Jitney bus from Jamesport to Manhattan. The 1 BR cottage includes complete kitchen, laundry, free parking, free swimming, tennis and basketball privileges at the Town Beach and one free wine tour.

Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 162 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)

Superhost

Cottage in Cutchogue

4.69 out of 5 average rating, 187 reviews

Lovely 2 BR Beach House No. Shore

Our adorable 2 BR cottage in the heart of wine country in LI's North Shore is impeccably decorated with a separate breezy, sunny dinning room and screened in porch and a Jacuzzi in our bathroom. We are less than 1/2 mile walking distance to two beaches or less via our kayak! Wifi. Please note that local Southold town ordinance requires a 14 night minimum stay. Please contact us to discuss. Please contact us about our off season rates. Unfortunately, we can no longer accept pets of any kind.

Guest favorite

Cottage in Montauk

4.92 out of 5 average rating, 144 reviews

Montauk Cottage Escape

EH Town Rental Registry #: 23-483 MINIMUM STAYS REQUIRED Updated, spacious and comfortably furnished home in Montauk. Well situated to get you most places on foot or bike. Less than 10 minute walk to town, beaches, restaurants, nightlife. Walk to Sole East where you can enjoy use of pool and have lunch or a cocktail. Great place to enjoy your time in Montauk. Additional nightly fees apply for 5th guest. Pets considered with prior owner approval (Dogs ONLY). Additional Pet Fee applies.

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 167 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Guest favorite

Cottage in East Hampton

5.0 out of 5 average rating, 32 reviews

Storybook Cottage Seconds to East Hampton Village

Beach Cottage at edge of East Hampton Village. This fresh and bright cottage with three bedrooms and two new bathrooms is a compact and convenient jewel box with everything you'd expect in the Hamptons - including a beautiful pool with built-in hot tub. Just blocks from the heart of East Hampton on a quiet no-traffic cul-de-sac, not far from beach, shopping, dining and train... sparkling kitchen with new 'retro style' appliances, gleaming hardwood floors throughout, and a cozy front porch.

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 105 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!

Guest favorite

Cottage in East Hampton

5.0 out of 5 average rating, 24 reviews

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 220 reviews

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

Guest favorite

Cottage in East Hampton

4.9 out of 5 average rating, 128 reviews

East Hampton Fisherman’s Cottage with Secret Room

This renovated cottage is located just a few minutes from East Hampton Village and is walking distance to Three Mile Harbor. This light filled home features wood flooring throughout, inviting living room with vaulted ceiling, an updated kitchen, two bathrooms (one with a secret entrance!) and a side yard with a brick patio, outdoor shower and hammock.