Holiday houses in Water Mill

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Top-rated holiday rentals in Water Mill

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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.

11 – 18 Sept

$3,844 AUD total

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!

24 – 31 Oct

$3,295 AUD total

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 164 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.

9 – 16 Oct

$5,968 AUD total

Guest favourite

Home in Sag Harbor

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with 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, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

11 – 18 June

$11,371 AUD total

Guest favourite

Home in Water Mill

4.92 out of 5 average rating, 91 reviews

Peaceful 1850s barn w/Pool

Family, friends and work-friendly property. Sleeps 8 (+2) in 4 bedrooms with 3 bathrooms. Tranquil 3000 sq ft house w/heated pool (pool season c. May 16 to Sept 20) set in 1.7 quiet acres off private driveway. Large garden and fenced pool area. Fresh in summer, cozy w/log fires in winter. Minutes from beautiful beaches, Water Mill's historic charm and the visual & performing arts. A simple but stylish and very comfortable house! Well-behaved pets with thoughtful owners are welcome.

26 Apr – 3 May

$9,488 AUD total

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 102 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!

29 Dec – 5 Jan

$10,815 AUD total

Superhost

Home in Water Mill

4.81 out of 5 average rating, 16 reviews

Charming Water Mill Get Away

Beautiful home on a quiet street. Immaculately maintained. In addition to five bedrooms and three bathrooms, this home boasts two living rooms and sunlight throughout to create a wonderfully bright feel. Country style kitchen for indoor cooking and a grill for outdoor BBQ's. Beautiful outdoor space with mature trees, lawn, a huge charming barn, teak garden furniture and a large swimming pool. Indoor movie theater and ping pong table. Your perfect Hampton's stay starts right here!

20 – 27 Dec

$6,203 AUD total

Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Harbor Heights

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).

13 – 20 Jan

$942 AUD total

Guest favourite

Cottage in Water Mill

4.98 out of 5 average rating, 56 reviews

Head of Pond House - Waterfront Cottage

Charming Cottage at Head of Pond House with lake access (and pool access as of Memorial Day) . Close to beaches, wineries, restaurants and all the Hamptons have to offer. One bedroom, and two king beds (one in the loft area), one bath cottage with WIFI and projector. Kitchen including fridge, stove, oven and dishwasher for your perfect weekend or weeklong getaway. Ideal for anyone looking for a peaceful oasis while close to all the action of the East End.

25 Oct – 1 Nov

$5,982 AUD total

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.

12 – 19 Oct

$4,760 AUD total

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.

22 – 29 Sept

$8,270 AUD total

Guest favourite

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

15 – 22 Oct

$4,093 AUD total