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

Sag Harbor Vacation Rentals

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Check prices for these dates

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

Our top choices for Sag Harbor vacation rentals

Iron/ironing board, WiFi (free), individually decorated

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (321 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 ￥46,770
￥57,724 total
includes taxes & fees
Sep 7 - Sep 8
Windward Shores Ocean Resort
Condo | 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 ￥48,352
￥69,308 total
includes taxes & fees
Sep 9 - Sep 10
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 ￥46,855
￥56,620 total
includes taxes & fees
Sep 7 - Sep 8
Montauk Manor
Apartment | Iron/ironing board, WiFi (free)

4. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (441 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 ￥32,202
￥38,507 total
includes taxes & fees
Sep 8 - Sep 9
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 ￥54,630
￥62,415 total
includes taxes & fees
Sep 7 - Sep 8
North Fork Resort
Apartment | WiFi (free), 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 ￥58,158
￥71,587 total
includes taxes & fees
Sep 7 - Sep 8
Driftwood Resort
Apartment | 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 ￥53,066
￥71,330 total
includes taxes & fees
Sep 9 - Sep 10
The Surf Club
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

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 ￥134,743
￥171,968 total
includes taxes & fees
Sep 7 - Sep 8
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"We stay here at least once every summer. The room was clean, great water pressure in shower, and had a handy fridge, coffee maker and microwave. A very pleasant stay!"
Theresa 1-night trip
Posted 1 hour ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Sag Harbor

Search for holiday rentals in Sag Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Sag Harbor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Sag Harbor!

Frequently asked questions

Can I find a vacation rental in Sag Harbor?

Yes, we give you a choice of vacation rentals in Sag Harbor close to Sag Harbor Whaling and Historical Museum, or you can go with a more secluded option if you want 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 vacation home rentals that Sag Harbor has to offer?

The Hampton Sack a cheerful relaxing beach cottage: You might like this vacation home rental near Sag Harbor. It is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Sag Harbor?

With 315 Expedia vacation rentals, you're sure 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 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 Havens Beach and Foster Memorial Town Beach.

What are vacation rentals like in Sag Harbor?

Vacation rentals are private properties you can book for several days or longer in Sag Harbor. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for families.