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Sagaponack Vacation Rentals

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Our top choices for Sagaponack vacation rentals

1. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is CA $345
CA $752 total
includes taxes & fees
Sep 27 - Sep 28
Charming Accommodations in the Hamptons

2. 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 CA $469
CA $913 total
includes taxes & fees
Oct 11 - Oct 12
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

3. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is CA $303
CA $459 total
includes taxes & fees
Oct 1 - Oct 2
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

4. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (323 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 CA $168
CA $230 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort

5. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is CA $160
CA $1,869 total
includes taxes & fees
Sep 27 - Sep 28
Year round Jacuzzi - Blackberry Home

6. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
The price is CA $303
CA $459 total
includes taxes & fees
Oct 1 - Oct 2
Safari Tent Glamping,S7-CedarPt, East Hampton, NY

7. 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 CA $345
CA $770 total
includes taxes & fees
Sep 27 - Sep 28
Lovely studio with AC in charming Sag Harbor

8. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
8.0 out of 10, Very good, (2 reviews)
"Camila was very communicative and helpful. The cottage clearly has a history of high traffic, and while it holds a certain rustic charm, it's undeniably showing its age. The property feels quite worn and tired, with fixtures and furnishings having seen better days. On the surface, the cottage was tidy upon arrival, but closer inspection revealed that it lacked a deep, thorough cleaning. While the main living areas were presentable, the corners, baseboards, and other area's not immediately...
United States
Anonymous traveller
The price is CA $157
CA $699 total
includes taxes & fees
Oct 4 - Oct 5
Steps to the beach | Seabreeze Cottage #3

9. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
The price is CA $339
CA $1,352 total
includes taxes & fees
Oct 8 - Oct 9
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (58 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $360
CA $411 total
includes taxes & fees
Oct 26 - Oct 27
North Fork Resort

11. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,407 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is CA $182
CA $235 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor

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 CA $799
CA $1,472 total
includes taxes & fees
Sep 26 - Sep 27
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

13. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Unit 1021: Studio | 2nd Floor-Pool View | Starfish
Napeague
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
United States
Liana T.
The price is CA $228
CA $591 total
includes taxes & fees
Sep 27 - Sep 28
Unit 1021: Studio | 2nd Floor-Pool View | Starfish

14. 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, (33 reviews)
"Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend! "
United States
Leigh E.
The price is CA $1,498
CA $3,243 total
includes taxes & fees
Oct 4 - Oct 5
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

15. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (251 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is CA $208
CA $283 total
includes taxes & fees
Oct 4 - Oct 5
Driftwood Resort

16. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is CA $1,269
CA $1,978 total
includes taxes & fees
Oct 18 - Oct 19
Lovely & Spacious Sag Harbor escape with heated pool

17. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 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 CA $190
CA $1,728 total
includes taxes & fees
Sep 29 - Sep 30
Beachfront Jacuzzi All Year - Black Swan Home

18. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (10 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
The price is CA $494
CA $825 total
includes taxes & fees
Sep 27 - Sep 28
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

19. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (452 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is CA $167
CA $206 total
includes taxes & fees
Oct 20 - Oct 21
Montauk Oceanside Suites
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.

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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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : Visitors like this Sagaponack vacation home rental. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals will I find in Sagaponack?

With 34 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 Ocean Road Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Wolffer Estates Vineyard and Madoo Conservancy 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.