Sagaponack Vacation Rentals

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Our top choices for Sagaponack vacation rentals

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $275
CA $374 total
includes taxes & fees
May 31 - Jun 1
Cliffside Resort Condominiums

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is CA $285
CA $363 total
includes taxes & fees
May 26 - May 27
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,341 reviews)
"Had a wonderful stay"
United States
Meghan
Montauk Manor

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.8 out of 10, Excellent, (13 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is CA $278
CA $318 total
includes taxes & fees
May 19 - May 20
North Fork Cottages & RV Resort

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is CA $213
CA $288 total
includes taxes & fees
May 18 - May 19
Driftwood Resort

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is CA $720
CA $979 total
includes taxes & fees
May 13 - May 14
Offshore Residences

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is CA $225
CA $272 total
includes taxes & fees
May 13 - May 14
Montauk Oceanside Suites

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (281 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is CA $229
CA $336 total
includes taxes & fees
May 19 - May 20
The Surf Club

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (16 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is CA $235
CA $1,737 total
includes taxes & fees
May 12 - May 13
Black Swan Beachfront Home with Jacuzzi year round

Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
The price is CA $609
CA $1,109 total
includes taxes & fees
May 12 - May 13
Lovely studio with AC in charming Sag Harbor

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is CA $286
CA $436 total
includes taxes & fees
May 26 - May 27
American Beech in Greenport - Petite King Room 7

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is CA $689
CA $1,275 total
includes taxes & fees
May 12 - May 13
Beachfront Greenport Villa

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (1 review)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is CA $260
CA $516 total
includes taxes & fees
Jun 1 - Jun 2
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is CA $2,043
CA $2,661 total
includes taxes & fees
May 12 - May 13
Cozy 5 Bedroom With Wi-fi And Air Condition

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is CA $818
CA $1,425 total
includes taxes & fees
May 18 - May 19
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Designer East Hampton Farmhouse - Bike to Amagansett, Ocean Beaches, Pool Open

Designer East Hampton Farmhouse - Bike to Amagansett, Ocean Beaches, Pool Open
East Hampton North
Designer East Hampton Farmhouse - Bike to Amagansett, Ocean Beaches, Pool Open

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is CA $1,368
CA $1,781 total
includes taxes & fees
May 12 - May 13
Cozy Hamptons Escape 3BR Minutes From Beach!

Seabreeze 4 Charming Cottage walk to US Open

Seabreeze 4 Charming Cottage walk to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $286
CA $848 total
includes taxes & fees
May 25 - May 26
Seabreeze 4 Charming Cottage walk to US Open

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, (15 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 CA $2,458
CA $3,436 total
includes taxes & fees
May 12 - May 13
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is CA $2,362
CA $3,700 total
includes taxes & fees
Jun 8 - Jun 9
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
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 Sagaponack Hotel Reviews

Find out more about Sagaponack

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sagaponack. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Sagaponack?

Yes, we have vacation rentals in Sagaponack close to Madoo Conservancy, or you can select a secluded option if you're looking for extra privacy while you relax. Sagaponack is known for its wineries and gardens. Make sure you have time to check out the beaches and shopping during your trip.

What are some of the best vacation home rentals that Sagaponack has to offer?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: Visitors like this Sagaponack vacation home rental. It offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Sagaponack?

With 37 Expedia vacation rentals, you're sure to find just the right place for your Sagaponack stay.

What can I see and do in Sagaponack?

The Hamptons Beaches and Madoo Conservancy are a couple of lovely local spots to get outside and enjoy nature. While here, Wolffer Estates Vineyard and SagPond Vineyards are other places worth a visit.

What are vacation rentals like in Sagaponack?

Vacation rentals are privately owned properties you can book for a long or short time in Sagaponack. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for small groups.