A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Sag Harbor Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Sag Harbor holiday rentals

Iron/ironing board, free WiFi, individually decorated

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 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 S$468
includes taxes & fees
7 Sept - 8 Sept
Windward Shores Ocean Resort
Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (281 reviews)
"Great place!"
United States
Christine
The price is S$562
includes taxes & fees
9 Sept - 10 Sept
Cliffside Resort Condominiums
Lobby

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,384 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is S$460
includes taxes & fees
7 Sept - 8 Sept
Montauk Manor
Iron/ironing board, free WiFi

4. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (442 reviews)
"The location is amazing, and the customer service is excellent. Unfortunately, the mattress and the air conditioning were the worst I’ve ever experienced, which made my stay much less comfortable."
United States
Carlos
The price is S$313
includes taxes & fees
8 Sept - 9 Sept
Montauk Oceanside Suites
Flat-screen TV

5. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (45 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is S$460
includes taxes & fees
10 Sept - 11 Sept
North Fork Resort
Free WiFi, individually decorated, individually furnished, bed sheets

6. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (245 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is S$581
includes taxes & fees
7 Sept - 8 Sept
Driftwood Resort
Living area

7. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (292 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is S$579
includes taxes & fees
9 Sept - 10 Sept
The Surf Club
Living area

8. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (3 reviews)
"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...
United States
Frank
The price is S$1,396
includes taxes & fees
7 Sept - 8 Sept
Offshore Spa & Residences
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

The Pridwin Hotel

The Pridwin Hotel

10/10 Excellent
"a"
Heather 1-night trip
Posted 6 hours ago
The Pridwin Hotel

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 317 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 Elizabeth A. Morton National Wildlife Refuge and The Hamptons Beaches are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Noyac Golf Club and Havens Beach.

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.