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

Sag Harbor Holiday Rentals

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Our top choices for Sag Harbor holiday rentals

1. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is NZ$868
includes taxes & fees
23 Nov - 24 Nov
Lovely studio with AC in charming Sag Harbor

2. Luxury Village Rental in the Heart of Sag Harbor

Luxury Village Rental in the Heart of Sag Harbor
Sag Harbor
The price is NZ$1,641
includes taxes & fees
23 Nov - 24 Nov
Luxury Village Rental in the Heart of Sag Harbor

3. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is NZ$1,954
includes taxes & fees
12 Nov - 13 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

4. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is NZ$3,670
includes taxes & fees
12 Nov - 13 Nov
Lovely & Spacious Sag Harbor escape with heated pool

5. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is NZ$868
includes taxes & fees
23 Nov - 24 Nov
Charming Accommodations in the Hamptons

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is NZ$586
includes taxes & fees
26 Nov - 27 Nov
Cliffside Resort Condominiums

7. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,425 reviews)
"We’ve been to Montauk Manor many times. The inside pool area is updated and nice to use. Gavin a restaurant there is quite convenient. The units are comfortable and lovely with fully stocked kitchens."
United States
barbara
The price is NZ$316
includes taxes & fees
30 Nov - 1 Dec
Montauk Manor

8. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (333 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is NZ$315
includes taxes & fees
15 Nov - 16 Nov
Windward Shores Ocean Resort

9. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is NZ$403
includes taxes & fees
22 Nov - 23 Nov
Harbor Heights

10. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is NZ$422
includes taxes & fees
30 Nov - 1 Dec
The SandPiper

11. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
Year round Jacuzzi - Blackberry East Hampton Home

12. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is NZ$410
includes taxes & fees
1 Dec - 2 Dec
Aqua Vista

13. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is NZ$632
includes taxes & fees
15 Nov - 16 Nov
North Fork Resort

14. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is NZ$589
includes taxes & fees
19 Nov - 20 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

15. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is NZ$984
includes taxes & fees
15 Nov - 16 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

16. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is NZ$800
includes taxes & fees
18 Nov - 19 Nov
Steps to the beach | Seabreeze Cottage #3

17. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is NZ$505
includes taxes & fees
22 Nov - 23 Nov
American Beech in Greenport - Petite King Room 7

18. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is NZ$758
includes taxes & fees
22 Nov - 23 Nov
Beach Block Hideaway

19. Cozy Cottage by the beach - Seabreeze #1

Cozy Cottage by the beach - Seabreeze #1
Hampton Bays
The price is NZ$788
includes taxes & fees
23 Nov - 24 Nov
Cozy Cottage by the beach - Seabreeze #1

20. Serene, chic East Hampton home - minutes to beaches, Main St., and so much more

Serene, chic East Hampton home - minutes to beaches, Main St., and so much more
East Hampton
The price is NZ$2,058
includes taxes & fees
23 Nov - 24 Nov
Serene, chic East Hampton home - minutes to beaches, Main St., and so much more
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sag Harbor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sag Harbor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sag Harbor. Seeing all the best attractions is bound to make you fall in love with Sag Harbor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sag Harbor short-term rentals, that won’t be hard to do.

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.

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

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This holiday home rental outside Sag Harbor offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Sag Harbor?

With 306 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 Noyac Golf Club and Elizabeth A. Morton National Wildlife Refuge.

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.