Holiday houses in Water Mill

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Top-rated holiday rentals in Water Mill

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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

$564 NZD per night

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 163 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.

23–30 Oct

$912 NZD per night

Guest favourite

Loft in Water Mill

5.0 out of 5 average rating, 12 reviews

Cozy ,Renovated Apartment for single or couple

Nice ,newly renovated basement apartment with natural light. high ceilings, walk out patio door, private entrance, soundproofed, washer/dryer, dishwasher , radiant heated bathroom floor, independent heating and cooling system from main house, off street parking for one vehicle, perfect for single or couple. Centrally located for all fall activities, farm stands, apple picking, Film Fest, Dining , shopping. This apartment has been vacant since last summer and since being renovated.

24–31 May

$496 NZD per night

Guest favourite

Cottage in Southampton

4.97 out of 5 average rating, 99 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!

16–23 Aug

$1,771 NZD per night

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!

30 Nov – 7 Dec

$1,020 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!

20–27 Aug

$1,108 NZD per night

Guest favourite

Home in Southampton

4.9 out of 5 average rating, 213 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

5–12 Jun

$1,034 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.

1–8 Feb

$736 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.

10–17 Oct

$1,323 NZD per night

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 circa May 21 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!

29 Oct – 5 Nov

$1,478 NZD per night

Guest favourite

Home in Water Mill

4.88 out of 5 average rating, 72 reviews

Charming Water Mill Cottage

This cottage is part of a compound consisting of a main house and pool house/studio. It has a King Size Bed in the bedroom; a Cozy Eat in Kitchen with a full size Stove and Microwave, along with a Full Size Fridge. There's plenty of seating in the Living-Room, that also has a pull out couch, as well as a Fully Tiled Bathroom. There's a large private patio with hedged in fence. It's the perfect space for relaxing.

26 Dec – 2 Jan

$421 NZD per night

Guest favourite

Cottage in Water Mill

4.98 out of 5 average rating, 55 reviews

Head of Pond House - Waterfront Cottage

Charming Cottage with lake access. 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.

28 Apr – 5 May

$888 NZD per night