Sag Harbor Holiday Rentals

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Holiday Rentals in Sag Harbor

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town
Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
9.0 out of 10, Wonderful, (2)
"Great location and comfortable stay, amazing sheets.Ended up buying for my home. "
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum
10.0 out of 10, Exceptional, (50)
"For our first time in the Hamptons, this location was perfect.we could walk most everywhere we needed.Exploring from this location was not a bad drive.A wonderful memory was made!!!!"
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
2.0 star property
7.0 out of 10, Good, (8)
"We had a fantastic stay! The home was exactly as described — clean and very comfortable. The location was perfect. We loved being close to town. Communication was smooth and easy — Frank was quick to respond. We’d absolutely stay here again and recommend it to anyone visiting the area! "
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
Luxury Resort-Style Retreat in the Heart of Sag Harbor with Heated Pool,...
10.0 out of 10, Exceptional, (1)
"beautiful place"
Luxury Resort-Style Retreat in the Heart of Sag Harbor with Heated Pool,...
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1253)
"Beautiful grounds, excellent staff"
The price is AU$385
includes taxes & fees
7 Nov - 8 Nov
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (298)
"Loved the balcony view….wrong season for swimming but pool looks inviting"
Windward Shores Ocean Resort
Montauk Oceanside Suites
3.0 star property
8.6 out of 10, Excellent, (415)
"We loved it, suite size was great! "
The price is AU$255
includes taxes & fees
20 Oct - 21 Oct
Montauk Oceanside Suites
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (243)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
The price is AU$459
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
The price is AU$302
includes taxes & fees
20 Oct - 21 Oct
Driftwood Resort
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
8.8 out of 10, Excellent, (28)
"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
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (280)
"Very close walk to the beach great for little ones "
The Surf Club
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
The price is AU$594
includes taxes & fees
27 Oct - 28 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
MONTAUK MANOR-DELUXE STUDIO APARTMENT
9.8 out of 10, Exceptional, (75)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (33)
"Enjoyed our stay"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"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
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (140)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
10.0 out of 10, Exceptional, (15)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is AU$512
includes taxes & fees
15 Oct - 16 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Offshore Residences
4.5 star property
The price is AU$1,102
includes taxes & fees
19 Oct - 20 Oct
Offshore Residences
The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is AU$257
includes taxes & fees
15 Oct - 16 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
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 Sag Harbor Hotel Reviews

Find out more about Sag Harbor

Everything you need to know about Sag Harbor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sag Harbor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sag Harbor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sag Harbor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sag Harbor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sag Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sag Harbor holiday rentals we have selected for you start as low as AU$255 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sag Harbor rentals

At Expedia, we put the best Sag Harbor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sag Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sag Harbor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sag Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Sag Harbor?

Yes, there are holiday rentals in Sag Harbor close to Sag Harbor Whaling and Historical Museum, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Sag Harbor is known for its waterfront. Make sure you have time to check out the beaches and churches during your trip.

What are some of the best holiday rentals that Sag Harbor has to offer?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This holiday home rental outside of Sag Harbor offers an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Sag Harbor?

With 321 Expedia holiday rentals, you're guaranteed to find just the right place for your Sag Harbor stay.

What can I see and do in Sag Harbor?

Cultural attractions include Sag Harbor Whaling and Historical Museum and Bay Street Theatre, whereas Havens Beach and Foster Memorial Town Beach are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Noyac Golf Club and The Style Bar.

What are holiday rentals like in Sag Harbor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sag Harbor. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family getaway.