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

Sag Harbor Vacation 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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Sag Harbor vacation 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 ￥35,712
￥78,882 total
includes taxes & fees
Nov 16 - Nov 17
Charming Accommodations in the Hamptons
A house with a sliding glass door, a white door, and a small porch with 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 ￥87,615
￥177,531 total
includes taxes & fees
Nov 13 - Nov 14
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern living room with a flat-screen TV, a dining table with chairs, a sofa, a coffee table, and a chandelier.

3. Luxury Village Rental in the Heart of Sag Harbor

Luxury Village Rental in the Heart of Sag Harbor
Sag Harbor
The price is ￥107,136
￥145,618 total
includes taxes & fees
Nov 13 - Nov 14
Luxury Village Rental in the Heart of Sag Harbor
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

4. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is ￥242,842
￥335,657 total
includes taxes & fees
Nov 15 - Nov 16
Lovely & Spacious Sag Harbor escape with heated pool
A small cabin with a porch, surrounded by trees and a fenced area.

5. 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 ￥35,712
￥78,882 total
includes taxes & fees
Nov 16 - Nov 17
Lovely studio with AC in charming Sag Harbor
A spacious hallway with high ceilings, arched columns, and chandeliers.

6. 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 ￥21,999
￥28,240 total
includes taxes & fees
Nov 30 - Dec 1
Montauk Manor
A balcony with a view of the ocean, a lawn, and a house in the background.

7. 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 ￥30,690
￥52,789 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums
Room

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 ￥20,913
￥28,208 total
includes taxes & fees
Nov 15 - Nov 16
Windward Shores Ocean Resort
A beach with people relaxing on chairs and sunbathing.

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 ￥13,571
￥35,454 total
includes taxes & fees
Nov 15 - Nov 16
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

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 ￥15,078
￥36,448 total
includes taxes & fees
Dec 3 - Dec 4
The SandPiper
A modern house with a deck, outdoor seating, and a fire pit.

11. 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 ￥48,957
￥55,935 total
includes taxes & fees
Nov 19 - Nov 20
North Fork Resort
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

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 ￥15,078
￥38,443 total
includes taxes & fees
Nov 18 - Nov 19
Aqua Vista
A residential driveway with a parked car, surrounded by greenery and a house.

13. 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 ￥45,235
￥88,677 total
includes taxes & fees
Nov 15 - Nov 16
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.

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 ￥20,713
￥55,217 total
includes taxes & fees
Nov 15 - Nov 16
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

15. 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 ￥9,515
￥72,092 total
includes taxes & fees
Nov 15 - Nov 16
Steps to the beach | Seabreeze Cottage #3
An outdoor dining area with hanging lights, palm trees, and a bar.

16. 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 ￥31,585
￥46,062 total
includes taxes & fees
Nov 15 - Nov 16
American Beech in Greenport - Petite King Room 7
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 ￥30,950
￥68,000 total
includes taxes & fees
Nov 15 - Nov 16
Beach Block Hideaway
A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

18. Cozy Cottage by the beach - Seabreeze #1

Cozy Cottage by the beach - Seabreeze #1
Hampton Bays
The price is ￥8,563
￥71,045 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Cottage by the beach - Seabreeze #1
A residential property with a covered patio, outdoor seating, and a hot tub.

19. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥9,696
￥181,491 total
includes taxes & fees
Nov 13 - Nov 14
Jacuzzi year-round - Villa Luz Private Home
A kitchen with a central island, white cabinetry, and a brick accent wall.

20. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (34 reviews)
"We loved this home and location! The home is so beautifully appointed and clean. It had everything you would ever need for a wonderful time with family and friends. The hosts were extremely responsive and easy to work with. We would go back in a heartbeat!"
United States
Suzanne B.
The price is ￥138,185
￥325,811 total
includes taxes & fees
Nov 17 - Nov 18
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
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

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"Great stay! Quiet and peaceful! Wonderful view of the ocean!"
Benjamin 2-night trip
Posted 1 day ago
Montauk Blue Hotel

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 vacation rental in Sag Harbor?

Yes, we give you a choice of vacation rentals in Sag Harbor close to Bay Street Theatre, 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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: You might like this vacation home rental near Sag Harbor. It offers an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Sag Harbor?

With 306 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 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 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.