Sag Harbor Vacation Rentals

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Our top choices for Sag Harbor vacation 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
$5,690 nightly
The price is $6,501
May 5 - May 6
Total with taxes and fees
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
$5,553 nightly
The price is $6,344
May 3 - May 4
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
$283 nightly
The price is $323
May 21 - May 22
Total with taxes and fees
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
$295 nightly
The price is $337
May 21 - May 22
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Waterfront Oasis • Minutes to US Open Golf • Sleeps 10 People

Waterfront Oasis • Minutes to US Open Golf • Sleeps 10 People
East Quogue
$12,564 nightly
The price is $14,354
May 7 - May 8
Total with taxes and fees
Waterfront Oasis • Minutes to US Open Golf • Sleeps 10 People

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
$187 nightly
The price is $214
May 3 - May 4
Total with taxes and fees
North Fork Cottages & RV Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,336 reviews)
"Incredible place to stay "
United States
melissa
$168 nightly
The price is $192
May 18 - May 19
Total with taxes and fees
Montauk Manor

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (41 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$168 nightly
The price is $190
May 1 - May 2
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
$183 nightly
The price is $209
May 3 - May 4
Total with taxes and fees
Windward Shores Ocean Resort

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$237 nightly
The price is $268
May 3 - May 4
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
$224 nightly
The price is $256
May 11 - May 12
Total with taxes and fees
Cliffside Resort Condominiums

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (55 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
$240 nightly
The price is $271
May 10 - May 11
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
$283 nightly
The price is $323
May 21 - May 22
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (423 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
$174 nightly
The price is $199
May 7 - May 8
Total with taxes and fees
Montauk Oceanside Suites

Seabreeze #4 Charming Cottage just 2.5 miles to US Open

Seabreeze #4 Charming Cottage just 2.5 miles to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$576 nightly
The price is $620
May 4 - May 5
Total with taxes and fees
Seabreeze #4 Charming Cottage just 2.5 miles to US Open

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
$184 nightly
The price is $211
May 17 - May 18
Total with taxes and fees
Driftwood Resort

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
$571 nightly
The price is $646
May 6 - May 7
Total with taxes and fees
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
$234 nightly
The price is $267
May 11 - May 12
Total with taxes and fees
The Surf Club

Hamptons apartment getaway

Hamptons apartment getaway
East Quogue
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
$257 nightly
The price is $294
May 1 - May 2
Total with taxes and fees
Hamptons apartment getaway

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"This is a must property for any vacationer traveling to Long Island. You will fall in love with quiet evenings after delightful beach walks. Don’t forget the therapeutic ocean air! Within very short walking distance, you are near The Pavilion and the famous Kokomo’s Restaurant. Kokomo’s is the best ocean restaurant in Old Lyme for a reason, with fantastic ocean views and an unmatched family dining experience. As Old Lyme begins its long-awaited restoration project, this beach apartment will...
United States
Jennivere
$255 nightly
The price is $288
May 3 - May 4
Total with taxes and fees
Keel at Soundview · Beach+OceanView+Sunrise
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sag Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sag Harbor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sag Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $190 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sag Harbor rentals

At Expedia, we put the best Sag Harbor vacation 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 vacation.

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 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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This vacation home near Sag Harbor offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Sag Harbor?

With 313 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 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 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.