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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Sag Harbor holiday rentals

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

1. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is HK$1,920
HK$4,191 total
includes taxes & fees
7 Sept - 8 Sept
Charming Accommodations in the Hamptons
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

2. 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 HK$6,578
HK$11,456 total
includes taxes & fees
2 Sept - 3 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A small cabin with a porch, surrounded by trees and a fenced area.

3. 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 HK$2,312
HK$4,809 total
includes taxes & fees
13 Sept - 14 Sept
Lovely studio with AC in charming Sag Harbor
A row of tents with a grassy field and trees in the background.

4. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is HK$1,516
HK$2,323 total
includes taxes & fees
2 Sept - 3 Sept
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
A row of tents with a grassy field and trees in the background.

5. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is HK$1,685
HK$2,543 total
includes taxes & fees
18 Sept - 19 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
A modern house with a deck, outdoor seating, and a fire pit.

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (52 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is HK$2,519
HK$2,877 total
includes taxes & fees
15 Sept - 16 Sept
North Fork Resort

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (290 reviews)
"Great place!"
United States
Christine
The price is HK$2,368
HK$3,404 total
includes taxes & fees
27 Sept - 28 Sept
Cliffside Resort Condominiums

8. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (248 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is HK$1,309
HK$1,751 total
includes taxes & fees
21 Sept - 22 Sept
Driftwood Resort
A beach with people relaxing on chairs and sunbathing.

9. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is HK$1,376
HK$2,817 total
includes taxes & fees
3 Sept - 4 Sept
Harbor Heights

10. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is HK$1,470
HK$1,893 total
includes taxes & fees
24 Sept - 25 Sept
Windward Shores Ocean Resort
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

11. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is HK$1,376
HK$2,718 total
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

12. 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, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is HK$2,234
HK$4,576 total
includes taxes & fees
20 Sept - 21 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A beach with people relaxing, a pier extending into the water, and a clear sky.

13. 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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is HK$1,376
HK$3,292 total
includes taxes & fees
8 Sept - 9 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden pathway leading to a beach with scattered rocks and greenery.

14. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is HK$1,529
HK$3,269 total
includes taxes & fees
7 Sept - 8 Sept
Beach Block Hideaway
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

15. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is HK$1,529
HK$2,911 total
includes taxes & fees
14 Sept - 15 Sept
Aqua Vista
A spacious living room with a large sofa, a round coffee table, and a television. A kitchen with a refrigerator and cabinets is visible in the background.

16. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
8.0 out of 10, Very good, (2 reviews)
"Camila was very communicative and helpful. The cottage clearly has a history of high traffic, and while it holds a certain rustic charm, it's undeniably showing its age. The property feels quite worn and tired, with fixtures and furnishings having seen better days. On the surface, the cottage was tidy upon arrival, but closer inspection revealed that it lacked a deep, thorough cleaning. While the main living areas were presentable, the corners, baseboards, and other area's not immediately...
United States
Anonymous traveller
The price is HK$870
HK$3,860 total
includes taxes & fees
2 Sept - 3 Sept
Seabreeze #3 Cozy Cottage steps to the beach
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

17. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$931
HK$1,799 total
includes taxes & fees
2 Sept - 3 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
An outdoor dining area with hanging lights, palm trees, and a bar.

18. 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 HK$2,344
HK$3,421 total
includes taxes & fees
8 Sept - 9 Sept
American Beech in Greenport - Petite King Room 7
A dining area with a round table, six chairs, and a chandelier.

19. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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.
The price is HK$3,355
HK$13,404 total
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes from the downtown area. Highly recommend this property."
Arabella 1-night trip
Posted 9 hours ago
Montauk Yacht Club

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:

  • View our selection of featured holiday rentals in Sag Harbor
  • Use the map to find apartments and other holiday homes in the Sag Harbor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sag Harbor while they last

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

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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Sag Harbor is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many holiday rentals are there in Sag Harbor?

With 314 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 Havens Beach 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 Foster Memorial Town 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.