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

Sag Harbor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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$1,766
HK$3,999 total
includes taxes & fees
19 Oct - 20 Oct
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$4,227
HK$9,107 total
includes taxes & fees
18 Oct - 19 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

3. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is HK$12,008
HK$17,467 total
includes taxes & fees
18 Oct - 19 Oct
Lovely & Spacious Sag Harbor escape with heated pool
A small cabin with a porch, surrounded by trees and a fenced area.

4. 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$1,766
HK$4,098 total
includes taxes & fees
19 Oct - 20 Oct
Lovely studio with AC in charming Sag Harbor
Terrace/patio

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is HK$1,326
HK$2,386 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
A beach with people relaxing on chairs and sunbathing.

6. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is HK$745
HK$1,955 total
includes taxes & fees
2 Nov - 3 Nov
Harbor Heights
A dining area with a round table, six chairs, and a chandelier.

7. 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.
The price is HK$487
HK$9,868 total
includes taxes & fees
18 Oct - 19 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

8. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 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 HK$746
HK$1,937 total
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

9. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is HK$746
HK$1,937 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

10. 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$2,236
HK$4,581 total
includes taxes & fees
4 Nov - 5 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Room

11. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (329 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 HK$1,094
HK$1,464 total
includes taxes & fees
25 Oct - 26 Oct
Windward Shores Ocean Resort
A beach with people relaxing, a pier extending into the water, and a clear sky.

12. 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, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is HK$1,138
HK$2,941 total
includes taxes & fees
2 Nov - 3 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Room

13. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is HK$1,075
HK$1,484 total
includes taxes & fees
19 Oct - 20 Oct
Driftwood Resort
A modern house with a deck, outdoor seating, and a fire pit.

14. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (66 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is HK$2,521
HK$2,880 total
includes taxes & fees
19 Oct - 20 Oct
North Fork Resort
An outdoor dining area with hanging lights, palm trees, and a bar.

15. 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$1,562
HK$2,403 total
includes taxes & fees
19 Oct - 20 Oct
American Beech in Greenport - Petite King Room 7
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

16. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is HK$1,491
HK$4,923 total
includes taxes & fees
25 Oct - 26 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A wooden pathway leading to a beach with scattered rocks and greenery.

17. 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 HK$1,530
HK$3,524 total
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A spacious hallway with high ceilings, arched columns, and chandeliers.

18. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,416 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is HK$1,147
HK$1,464 total
includes taxes & fees
17 Nov - 18 Nov
Montauk Manor
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

19. 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 HK$596
HK$3,544 total
includes taxes & fees
25 Oct - 26 Oct
Steps to the beach | Seabreeze Cottage #3
A spacious living area with a large bed, a dining table, and a kitchen in the background.

20. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Unit 1021: Studio | 2nd Floor-Pool View | Starfish
Napeague
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
United States
Liana T.
The price is HK$1,264
HK$3,272 total
includes taxes & fees
18 Oct - 19 Oct
Unit 1021: Studio | 2nd Floor-Pool View | Starfish
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sag Harbor Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Very clean bathroom. Very dated and weathered furniture. The linens were good. The paint on the door needed cleaned. The receptionist was very personable. We were on the first level and could hear the folks above."
kimberly 1-night trip
Posted less than an 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:

  • 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?

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.