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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Sag Harbor holiday rentals

Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,353 reviews)
"Had a wonderful stay"
United States
Meghan
The price is 7.089.440 ₫
8.615.342 ₫ total
includes taxes & fees
10 Jun - 11 Jun
Montauk Manor
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
"Great stay & great staff!"
United States
James
The price is 7.821.792 ₫
8.936.399 ₫ total
includes taxes & fees
15 Jun - 16 Jun
North Fork Resort
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is 5.356.479 ₫
7.264.259 ₫ total
includes taxes & fees
1 Jun - 2 Jun
Cliffside Resort Condominiums
Apartment | Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (240 reviews)
"Very close to beach"
United States
Rabia
The price is 4.987.248 ₫
6.555.820 ₫ total
includes taxes & fees
1 Jun - 2 Jun
Driftwood Resort
Apartment | Iron/ironing board, free WiFi

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 5.377.541 ₫
6.430.551 ₫ total
includes taxes & fees
1 Jun - 2 Jun
Montauk Oceanside Suites
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (313 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 5.404.411 ₫
6.890.815 ₫ total
includes taxes & fees
31 May - 1 Jun
Windward Shores Ocean Resort
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4/10 Poor
"major construction would be ongoing for three of our four days at the hotel. Had we been informed beforehand, we would have made different arrangements entirely. The first room we were assigned had multiple issues: The AC was not functioning, and the room was 80 degrees upon arrival. The “ocean view” room primarily overlooked the parking lot, where delivery and work trucks created noise throughout the day. The door hinge was broken, leaving visible openings to the outside where bugs could enter. We attempted to contact the front desk to request a room change but were unable to get through initially and received no callback. After calling again two hours later, we were told someone would bring new room keys. Thirty minutes passed with no follow-up, and when I called again, the front desk member appeared unaware of the situation entirely but was able to send someone. While we appreciated being moved, the second room also felt poorly maintained, with visible grime on the side table and floor. At that point, we did not want to continue complaining so did not raise the issue. Additionally, despite my emailed request ahead of arrival (below), there were no extra pillows in either room to support my pregnancy. Unfortunately, the issues extended throughout the property: The gym was incredibly warm, construction noise was so loud it could be heard through noise-canceling headphones, and three of the five treadmills were out of service. The fire pit and shared outdoor areas were d"
Kristen 3-night trip
Posted 4 hours ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

Can I find a holiday rental in Sag Harbor?

Yes, there are holiday rentals in Sag Harbor close to Bay Street Theatre, 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.

How many holiday rentals are there in Sag Harbor?

With 315 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 Bay Street Theatre and Sag Harbor Whaling and Historical Museum, whereas The Hamptons Beaches and Havens Beach are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Foster Memorial Town Beach and Noyac Golf Club.

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.