Holiday rentals with outdoor seating in Water Mill

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Water Mill

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

30 Jun – 7 Jul

$707 NZD per night

Guest favourite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 146 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

28 Nov – 5 Dec

$988 NZD per night

Guest favourite

Guesthouse in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

6–13 Oct

$558 NZD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 120 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

15–22 Oct

$1,230 NZD per night

Guest favourite

Apartment in Sag Harbor

4.98 out of 5 average rating, 132 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!

9–16 Oct

$611 NZD per night

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 100 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!

10–17 Aug

$1,660 NZD per night

Guest favourite

Home in Southampton

4.91 out of 5 average rating, 179 reviews

Peaceful Hamptons Cottage

Looking for a getaway? Nestled into one of the largest preserves in the Hamptons, this sunny newly renovated beachy cottage is the perfect retreat. The legendary Hamptons beaches, wineries, Southampton Village, and the world famous golf courses are less than a 10 minute drive away. There are many nearby essential shops, farm stands & restaurants. Set up for WFH with hi-speed wifi and a desk. Abuts a large nature preserve with hiking paths. Lots of deer will roam by your window!

14–21 Jul

$1,103 NZD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

15–22 Jan

$229 NZD per night

Guest favourite

Guest suite in Sag Harbor

4.95 out of 5 average rating, 188 reviews

Cedar Haven In Sag Harbor

This is a large one room studio apartment with private entrance and ensuite bathroom. The unit is private and closed off from the host’s house. The large main room has a queen bed, and a spacious seating area that includes chairs as well as a comfy leather couch. PLEASE NOTE: One night stays are welcomed but there is a higher rate: IN season, (June 1 - Oct 31) the ONE NIGHT RATE is $375 OFF season, (mid Oct - end of May) the ONE NIGHT RATE is $300

28 Aug – 4 Sep

$459 NZD per night

Guest favourite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

24–31 Mar

$732 NZD per night

Guest favourite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

27 Oct – 3 Nov

$1,317 NZD per night

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

4–11 Dec

$936 NZD per night