Water Mill Vacation Rentals

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Sep 25 - Sep 26
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Sep 26 - Sep 27
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Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Water Mill

Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (295)
"Very nice & affordable "
The price is ￥19,609
￥25,640 total
includes taxes & fees
Oct 19 - Oct 20
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is ￥38,707
￥50,690 total
includes taxes & fees
Oct 2 - Oct 3
Cliffside Resort Condominiums
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.8 out of 10, Excellent, (27)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (232)
"Great place to stay for small family "
The price is ￥19,841
￥27,516 total
includes taxes & fees
Sep 29 - Sep 30
Driftwood Resort
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (15)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is ￥25,906
￥58,943 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

9.8 out of 10, Exceptional, (31)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (74)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (189)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is ￥66,299
￥121,825 total
includes taxes & fees
Oct 2 - Oct 3
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
Southampton cozy cottage by the beach
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Cannot say enough good things. Unique, sprawling, beautiful property with more than enough room for a large group. Endless entertainment, great pool, walking distance from a few bars and restaurants. Great communication and accommodation from our host. Would recommend and rent again."
10 Bedroom Hampton House with a regulation size Pickleball court
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Terrace/patio

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
Terrace/patio

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

8.8 out of 10, Excellent, (3)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
The price is ￥29,857
￥39,003 total
includes taxes & fees
Oct 2 - Oct 3
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
Fabulous Waterfront Property in the Heart of Wine Country
Sun loungers, beach towels

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (181)
"Beautiful view, clean house, great location "
Fabulous Waterfront Property in the Heart of Wine Country
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Property grounds

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (97)
"My husband and I brought our puppy. He had a great time running around the yard and beach. We enjoyed our stay and hope to return. The property is beautiful and we were very happy to find a pet friendly place on the water and close to town."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.
TV, fireplace

Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.

The price is ￥82,071
￥434,428 total
includes taxes & fees
Sep 30 - Oct 1
Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Outdoor pool, a heated pool

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

10.0 out of 10, Exceptional, (88)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Stunning Hampton Holiday Family Fantasy for your Team
TV, fireplace, video library, stereo

Stunning Hampton Holiday Family Fantasy for your Team

10.0 out of 10, Exceptional, (72)
"We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. "
Stunning Hampton Holiday Family Fantasy for your Team
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.4 out of 10, Very Good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is ￥73,657
￥134,579 total
includes taxes & fees
Sep 30 - Oct 1
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (136)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
A heated pool

2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!

10.0 out of 10, Exceptional, (90)
"Beautiful house , with pool and amazing backyard, perfect to chill with your friends and family ! "
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
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
"Huge second floor suite. Full size fridge freezer and microwave. Excellent shower. Super comfortable beds. All spotlessly clean. Added bonus of an outdoor pool. Would not hesitate to stay in this hotel again. "
James 2-night trip
Posted 12 hours ago
The Bentley Hotel Southampton

Find out more about Water Mill

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:

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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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This vacation home rental near Water Mill offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Water Mill?

Expedia has 112 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 Atlantic Golf Course 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.