Holiday Rentals in Sag Harbor

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Our top choices for Sag Harbor holiday rentals

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is €5,594
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious 5-bedroom house with water views and 2 houses from the bay.

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is €5,558
includes taxes & fees
2 Jan - 3 Jan 2026
Sag Harbor Water View w Dock 1.5ml from town

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1275)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is €151
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is €6,342
includes taxes & fees
5 Jan - 6 Jan 2026
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is €168
includes taxes & fees
3 Jan - 4 Jan 2026
The Stern at Soundview · Beach+Ocean+Sunrise

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is €167
includes taxes & fees
29 Jan - 30 Jan 2026
1-bedroom cottage with Grove Beach 🏖️ access.

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is €387
includes taxes & fees
22 Jan - 23 Jan 2026
Seabreeze #3: Cozy Cottage by the beach

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is €1,108
includes taxes & fees
5 Jan - 6 Jan 2026
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is €383
includes taxes & fees
5 Jan - 6 Jan 2026
Beachside Bliss w/ Game Room, Gym & Golf Green

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4)
"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 €795
includes taxes & fees
4 Jan - 5 Jan 2026
Blackberry: Private home with jacuzzi year-round

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is €363
includes taxes & fees
1 Jan - 2 Jan 2026
Adorable Cottage, 5 min walk to water & town

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is €1,107
includes taxes & fees
4 Jan - 5 Jan 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub

Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub
Napeague
10.0 out of 10, Exceptional, (1)
"Great stay. Unfortunately, they told us there was pickleball but there wasn’t. "
United States
Kevin C.
The price is €673
includes taxes & fees
28 Jan - 29 Jan 2026
Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub

My Humble Abode 2BR Beachside Home | TennisPoolPKG

My Humble Abode 2BR Beachside Home | TennisPoolPKG
Napeague
10.0 out of 10, Exceptional, (1)
The price is €1,294
includes taxes & fees
27 Jan - 28 Jan 2026
My Humble Abode 2BR Beachside Home | TennisPoolPKG

Luxurious 3 BR Cottage w/ Ocean View Balcony

Luxurious 3 BR Cottage w/ Ocean View Balcony
Napeague
10.0 out of 10, Exceptional, (3)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
The price is €1,794
includes taxes & fees
26 Jan - 27 Jan 2026
Luxurious 3 BR Cottage w/ Ocean View Balcony

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
Bridgehampton
9.6 out of 10, Exceptional, (16)
"Wonderful & perfect for my pup and I. I’d go back!"
United States
Scott C.
The price is €402
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
8.0 out of 10, Very good, (2)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is €168
includes taxes & fees
4 Jan - 5 Jan 2026
The Anchor at Soundview · Beach+Ocean+Sunrise

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is €449
includes taxes & fees
7 Jan - 8 Jan 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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

Everything you need to know about Sag Harbor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sag Harbor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sag Harbor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sag Harbor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sag Harbor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sag Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sag Harbor holiday rentals we have selected for you start as low as €151 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sag Harbor rentals

At Expedia, we put the best Sag Harbor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sag Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sag Harbor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sag Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Sag Harbor?

Yes, there are holiday rentals in Sag Harbor close to Sag Harbor Whaling and Historical Museum, 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.

How many holiday rentals are there in Sag Harbor?

With 309 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 Off the Rocker.

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.