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)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1250)
"I had the best time and highly recommend this hotel!"
The price is NZ$622
includes taxes & fees
24 Oct - 25 Oct
Montauk Manor

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (295)
"Very nice & affordable "
The price is NZ$299
includes taxes & fees
19 Oct - 20 Oct
Windward Shores Ocean Resort

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (414)
"We loved it, suite size was great! "
The price is NZ$288
includes taxes & fees
20 Oct - 21 Oct
Montauk Oceanside Suites

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 NZ$590
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (277)
"Very close walk to the beach great for little ones "
The price is NZ$629
includes taxes & fees
29 Sept - 30 Sept
The Surf Club

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (232)
"Great place to stay for small family "
The price is NZ$380
includes taxes & fees
5 Oct - 6 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

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

9.8 out of 10, Exceptional, (32)
"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

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 NZ$704
includes taxes & fees
1 Oct - 2 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (13)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is NZ$580
includes taxes & fees
26 Oct - 27 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

9.8 out of 10, Exceptional, (95)
"Very Nice stay there for business would go back for pleasure"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

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!

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

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (74)
"The room was very nicely decorated and clean and had everything you would need. We enjoyed our stay here and appreciated not having to bring linens and towels to a vrbo rental. The only issues we faced not booking directly with the hotel was not being able to use hotel shuttle to town and we ran out of toilet paper and the front desk said they are not supoosed to provide it as we didnt book through them. Other than that the property is very nice providing seating outside to enjoy a beautiful...
MONTAUK MANOR-DELUXE STUDIO APARTMENT

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.

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

9.8 out of 10, Exceptional, (98)
"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 .

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 NZ$1,580
includes taxes & fees
29 Sept - 30 Sept
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
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

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 favorite 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 depends 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 NZ$288 per night. Entering your travel dates in the search wizard you might find 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?

Sag Harbor Water View w Dock 1.5ml from town: This highly rated holiday home rental in Sag Harbor is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease 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 balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Sag Harbor?

With 320 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 The Hamptons Beaches and Havens 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.