Holiday rentals in Sag Harbor Yacht Club

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Top-rated holiday rentals in Sag Harbor Yacht Club

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Guest favourite
A charming two-story house features a light exterior with contrasting blue shutters. A white picket fence with hydrangea plants encloses the front yard, while trees provide shade. The sloped roof adds character, and the surrounding greenery enhances the home's inviting presence.
Home in Sag Harbor
4.9 out of 5 average rating, 113 reviews

Walk to Village Sag Harbor Victorian

Charming 2 bedroom 2 bathroom house in the historic Village of Sag Harbor with view of pond and park. Walking distance (not driving) to the quaint village with restaurants, shops, long wharf, gym, yoga. Living room with fireplace, dining room, kitchen and office. Upstairs loft ensuite bedroom and bathroom. Downstairs bedroom and full bath with tub and shower. Flower filled back deck with BBQ. Wireless internet, 2 TV's, air conditioner units, washer dryer. Minutes to ocean and bay beaches.

Guest favourite
A classic two-story house with a wooden exterior is framed by neatly trimmed greenery. The front porch features a white gate, inviting guests. Views of the water and trees are visible in the background, suggesting a serene location.
Flat in Sag Harbor
4.91 out of 5 average rating, 171 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Guest favourite
A charming outdoor area features a black cottage in the background, with large glass doors reflecting the surroundings. The deck is adorned with potted red geraniums and wooden seating. A hot tub is positioned adjacent to the cottage, emphasizing a tranquil retreat atmosphere.
Guest house in Southampton
4.97 out of 5 average rating, 114 reviews

5 Star Rated Private Cottage Southampton/Sag Hrbr

The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.

Top guest favourite
Home in East Hampton
4.93 out of 5 average rating, 14 reviews

Sunlit cozy cottage by the bay.

Kick back and relax in this calm, stylish space.This serene and light-filled cottage in the heart of historic Springs has been thoughtfully restored using sustainable materials and modern amenities. Just a short walk from Maidstone Beach and beloved local spots like the Springs Tavern and the charming S and S Corner coffee shop, this peaceful retreat blends minimalist elegance with high-end comfort.The cottage is stocked with organic linens and luxurious down duvets for a restful nights.

Top guest favourite
A charming orange house with white shutters features a welcoming front entry. Four large windows, adorned with flower boxes, enhance the inviting appearance. Lush greenery surrounds the front yard, complemented by neatly trimmed bushes and a pathway leading to the entrance.
Flat in Sag Harbor
4.99 out of 5 average rating, 221 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Top guest favourite
The sleeping area features a plush bed with white bedding and two neatly arranged pillows. Warm light from the wall-mounted lamps illuminates the space, while green foliage is visible through the large windows on either side, creating a soothing atmosphere.
Flat in East Hampton
4.98 out of 5 average rating, 54 reviews

The Hideaway | Clearwater Beach

Your private retreat in the heart of Clearwater Beach, East Hampton! Escape to this serene, design-forward suite nestled in one of the most peaceful corners of the Hamptons. Just minutes from the bay, this luxury hideaway offers the perfect balance of comfort, style and convenience. The space features a plush king bed and all the amenities you need for a relaxing stay. Sip your morning coffee in your private outdoor space before heading off for a swim at Clearwater Beach.

Top guest favourite
An inviting outdoor sitting area features wooden chairs positioned near French doors. The space is surrounded by lush greenery, and a stone pathway leads to the entrance of the studio apartment. Flowering vines and potted plants add a touch of nature.
Guest suite in Sag Harbor
4.9 out of 5 average rating, 395 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

Top guest favourite
Flat in Sag Harbor
4.94 out of 5 average rating, 142 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Top guest favourite
Home in Sag Harbor
5 out of 5 average rating, 101 reviews

Sag Harbor Village Gem

Sag Harbor Village Gem. 3 br, 2.5 ba., Enclosed Porch, Great Room with Fireplace, Charming Patio and Yard, Grill, Garage. Nicely landscaped property. House is immaculate. Spacious Master Bedroom with high ceiling. All bedrooms have beautiful dressers and TVs. Washer / Dryer. 10 minute drive to Ocean Beaches and 1 to 2 minute drive to Harbor Beach. 8 to 10 minute stroll to heart of Sag Harbor Village Main St.

Top guest favourite
Cottage in Greenport
5 out of 5 average rating, 59 reviews

3 Min Walk to Beach| 1 Mile to Town | Fam-Friendly

<b>The Greenport Beach Cottage</b> • Bright & updated 800 sq ft coastal cottage • 3 minute walk to beach, 4 minute drive to town • Sleeps up to 5 guests • Family-Friendly Amenities • Backyard with 2 fire pits, charcoal & gas grill, outdoor shower • Garage with 4 beach cruiser bikes, Foosball table & small gym area Book your coastal getaway now- only a few summer weekends remaining! IG: @thegreenportbeachcottage

Guest favourite
A charming studio cottage is framed by lush greenery, featuring a well-maintained garden with blooming flowers and shrubs. Two white Adirondack chairs sit on the grass, inviting relaxation. A small air conditioning unit is visible in the cottage window, enhancing comfort during warmer days.
Guest house in Sag Harbor
4.83 out of 5 average rating, 146 reviews

Sag Harbor Cottage in historic district

Charming studio cottage in the historic district of Sag Harbor. Comfortable queen bed. Walk to shops or restaurants downtown. Nearby beaches for swimming, kayaking or sailing. Great location to explore all of the Hamptons or get to know Sag Harbor with its unique charm and friendly atmosphere. We are the "un-Hamptons."

Guest favourite
A modern kitchen features light cabinetry and natural stone backsplash, with stainless steel appliances. A spacious island with a countertop provides additional workspace. Natural light enters through the window, highlighting the kitchen's clean lines and organized layout.
Home in Sag Harbor
4.86 out of 5 average rating, 167 reviews

Sag Harbor House for rent.

3 bedroom 2 bath Cape Cod less than 1 mile to the great village of Sag Harbor. Brand new kitchen. Beautiful beaches are just a short drive or jog away. Perfect getaway spot where you can walk or cycle to town or beach. BBQ out back or walk into town for a bite.

Popular amenities for Sag Harbor Yacht Club holiday rentals