A wooden cabin by a calm river with a house in the background.

Water Mill Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Water Mill vacation rentals

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

1. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is ￥35,620
￥80,667 total
includes taxes & fees
Oct 13 - Oct 14
Charming Accommodations in the Hamptons
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

2. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is ￥27,071
￥95,320 total
includes taxes & fees
Oct 13 - Oct 14
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

3. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is ￥45,118
￥92,967 total
includes taxes & fees
Nov 1 - Nov 2
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

4. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is ￥13,615
￥72,509 total
includes taxes & fees
Oct 18 - Oct 19
Steps to the beach | Seabreeze Cottage #3
A small cabin with a porch, surrounded by trees and a fenced area.

5. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is ￥35,620
￥82,657 total
includes taxes & fees
Oct 13 - Oct 14
Lovely studio with AC in charming Sag Harbor
Terrace/patio

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is ￥26,758
￥48,135 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums
Room

7. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (326 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is ￥22,081
￥29,531 total
includes taxes & fees
Oct 18 - Oct 19
Windward Shores Ocean Resort
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

8. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is ￥71,240
￥175,625 total
includes taxes & fees
Oct 13 - Oct 14
Minutes from the beach, brand new 4 bedroom
A modern living room with a sofa, armchairs, a coffee table, and a TV.

9. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is ￥79,155
￥185,935 total
includes taxes & fees
Nov 2 - Nov 3
Minutes from the beach, brand new 3 bedroom
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

10. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is ￥90,712
￥197,945 total
includes taxes & fees
Oct 20 - Oct 21
Amazing Southampton Home with Private Heated Pool
A modern house with a deck, outdoor seating, and a fire pit.

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥37,957
￥43,367 total
includes taxes & fees
Oct 21 - Oct 22
North Fork Resort
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

12. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is ￥85,274
￥183,703 total
includes taxes & fees
Oct 13 - Oct 14
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

13. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is ￥8,707
￥67,298 total
includes taxes & fees
Oct 13 - Oct 14
Walk to Beach | Seabreeze Cottage #4
A tented accommodation with a bed, a small table, and a chair.

14. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Outstanding place"
United States
Michael H.
Safari Tent Glamping,S2-CedarPt, East Hampton, NY
A modern building with large windows overlooking a beach.

15. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is ￥17,256
￥188,794 total
includes taxes & fees
Oct 13 - Oct 14
Beachfront Jacuzzi All Year - Black Swan Home
A wooden house with a front porch, white railings, and a double door.

16. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is ￥338,435
￥462,349 total
includes taxes & fees
Oct 13 - Oct 14
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A wooden gate partially covered by lush green ivy.

17. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (16 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is ￥337,739
￥457,157 total
includes taxes & fees
Oct 13 - Oct 14
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A kitchen with a central island, white cabinetry, and a brick accent wall.

18. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (34 reviews)
"Loved it! Thank you for having us."
United States
Vera P.
The price is ￥178,732
￥377,476 total
includes taxes & fees
Nov 12 - Nov 13
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Room

19. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is ￥18,685
￥26,504 total
includes taxes & fees
Oct 13 - Oct 14
Driftwood Resort
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

20. Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is ￥142,337
￥243,649 total
includes taxes & fees
Oct 13 - Oct 14
Newly Renovated Pristine Southampton Colonial
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Water Mill Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"WOW What a nice hotel. Perfect location for Hampton Bays & Southampton. Very clean, very modern & very nice"
Doug 1-night trip
Posted 3 hours ago
The Bentley Hotel Southampton

Find out more about Water Mill

Search for holiday rentals in Water Mill on Expedia! You can easily find your home rentals, villas, holiday apartments in Water Mill using one of the methods below:

  • View our selection of featured holiday rentals in Water Mill
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Look no further and take a look at our great range of rental properties in Water Mill!

Frequently asked questions

Can I find a vacation rental in Water Mill?

Yes, we have vacation rentals close to popular sights in Water Mill, or you can select a more remote option if you're looking for relaxation. Water Mill is known for its theaters and live music. Make sure you have time to check out the art and wineries during your trip.

What's the top vacation rental that Water Mill has to offer?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This vacation home rental near Water Mill offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Water Mill?

Expedia has 115 vacation rentals for your stay in Water Mill.

What can I see and do in Water Mill?

The Hamptons Beaches and Mecox Bay are a couple of scenic spots to enjoy the outdoors, whereas Parrish Art Museum is one of the cultural attractions. Duck Walk Vineyards and Mill Pond are other places to visit while you're in town.

What are vacation rentals like in Water Mill?

Vacation rentals are private properties you can stay in for several days or longer in Water Mill. Vacation rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.