Holiday rentals with a patio in Sag Harbor

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Top-rated rentals with patio in Sag Harbor

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Guest favourite

Cottage in Sag Harbor

5.0 out of 5 average rating, 30 reviews

Luxury Gem At The Heart of Sag Harbor Village

An impeccably renovated, luxury cottage at the heart of Sag Harbor village. Walkable within minutes to the downtown shops, restaurants, marinas and local beach! In one of the most coveted historic streets, enjoy this two-bedroom house, its large living & dining rooms, two fireplaces, designer kitchen (and latest appliances). Countless details and gorgeous wide planked floors, mixed with technology throughout the house. The private backyard has a brick patio, landscaped garden and outdoor shower.

24 Jun – 1 Jul

€ 772 per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 18 reviews

Southampton Stunner: Pool, Beach & more!

Beautiful light and airy modern home, nestled in amongst the trees on a beautiful private property. Ideally situated between Southampton and Sag Harbor and walking distance to a beautiful beach and nature trails. Designer chic, but comfortable for all. Hi speed wifi, streaming services, beach gear, and more! Huge private yard with large in-ground swimming pool, lounge chairs, expansive deck w/grill, sweet balcony and separate 2 car garage. Truly the perfect place for your east end summer.

7–14 Dec

€ 802 per night

Guest favourite

Guest suite in Bridgehampton

4.92 out of 5 average rating, 48 reviews

Bridgehampton New & Modern Design

Located about a mile away from downtown Bridgehampton and less than three miles away from downtown Sag Harbor. This brand new unit includes everything. Everything in this unit is brand new and of high quality. The unit has its own separate parking area and entrance and it totally private from the main house. POOL AND HOT TUB USE WILL BE AVILABLE FOR MOST OF THE YEAR, use of the pool and hot tub amenities will be made available. The pool is now open for the season as of March24.

8–15 Jul

€ 769 per night

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 101 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!

26 Dec – 2 Jan

€ 900 per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 34 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

10–17 Feb

€ 732 per night

Guest favourite

Home in Sag Harbor

4.96 out of 5 average rating, 24 reviews

The Hamptons Casita: Modern Elegance with Pool

Welcome to The Hamptons Casita! Our newly-renovated home is ready to greet you this summer for month-long stays. Envisioned by award-wining architectural firm Sommet, this house was designed to have all modern conveniences in a coastal setting that expands through two floors, 3 main decks, a pool and a rooftop deck. We are close to Foster Memorial Beach, many wineries including Wolffer Estate Vineyard, and historic downtown Sag Harbor with its fantastic dinning and shopping.

3–10 Jun

€ 955 per night

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 71 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

12–19 Oct

€ 976 per night

Guest favourite

Guest house in Sag Harbor

5.0 out of 5 average rating, 6 reviews

Romantic studio cottage; Walk to town

A romantic hideaway in Sag Harbor's historic district, within easy walking distance of Main Street. This sweet studio guesthouse is perfect for two, with its own private entrance. In addition to the studio living space, it features a kitchenette, full bathroom (shower only), electric fireplace, and queen-size sofa-bed with plush memory foam topper. Free WiFi included. PLEASE NOTE: The studio is available for weekends/short stays only; no week-long or longer stays.

8–13 Dec

€ 417 per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 20 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.

8–15 Dec

€ 367 per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 7 reviews

Sag Harbor Dream Home: Heated Pool

Just minutes from Main Sreet in Sag Harbor, Long Beach, Wolffer Vineyard, and Sagg Main Beach, this home is a perfectly located, brand-new gut remodel, with over 3500sqft interior and an entertainer's dream yard - on a quiet cul-de-sac street. A stylish experience at this centrally-located escape! Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

23–30 Dec

€ 830 per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 57 reviews

Dream home in SH with Heated Pool OPEN from May 4

Beautiful three bedroom-three bathroom house situated on almost an acre. This newly renovated stylish home is located in North Sea - 1 mile drive to the Bay. Perfect for a relaxing get-away this Fall/Winter and for the upcoming Spring/Summer. Heated Pool is available/open from May 17th to first weekend of October (October 6 - 2024)

27 Jan – 3 Feb

€ 529 per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 22 reviews

Renovated Southampton Home+Pool

Welcome to our newly renovated 3-bedroom retreat in Southampton! With a pool, dedicated office, and room for 8 adults, it's perfect for families or friends. Just 5 mins from Southampton Village and 10 mins from the beach, it offers a blend of comfort and convenience. Book now and make unforgettable memories in Southampton!

3–10 May

€ 405 per night