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
$5,705 nightly
The price is $6,518
Dec 31 - Jan 1, 2026
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
$5,596 nightly
The price is $6,393
Dec 29 - Dec 30
Total with taxes and fees
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, (1272)
"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
$156 nightly
The price is $178
Jan 12 - Jan 13, 2026
Total with taxes and fees
Montauk Manor

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$391 nightly
The price is $447
Jan 20 - Jan 21, 2026
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the 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
$172 nightly
The price is $195
Jan 3 - Jan 4, 2026
Total with taxes and fees
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.
$172 nightly
The price is $194
Jan 5 - Jan 6, 2026
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

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.
$1,114 nightly
The price is $1,273
Jan 1 - Jan 2, 2026
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
$579 nightly
The price is $662
Dec 28 - Dec 29
Total with taxes and fees
Offshore Residences

My Humble Abode 2BR Beachside Home | TennisPoolPKG

My Humble Abode 2BR Beachside Home | TennisPoolPKG
Napeague
10.0 out of 10, Exceptional, (1)
$1,345 nightly
The price is $1,507
Jan 14 - Jan 15, 2026
Total with taxes and fees
My Humble Abode 2BR Beachside Home | TennisPoolPKG

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.
$445 nightly
The price is $503
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green

Your Quietude 1BR Beachside Home |Tennis+Pool+WiFi

Your Quietude 1BR Beachside Home |Tennis+Pool+WiFi
Napeague
10.0 out of 10, Exceptional, (1)
"Love place to stay. The beach was amazing "
United States
Brett
$769 nightly
The price is $862
Jan 13 - Jan 14, 2026
Total with taxes and fees
Your Quietude 1BR Beachside Home |Tennis+Pool+WiFi

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.
$509 nightly
The price is $582
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Saybrook Manor
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
United States
Deana L.
$511 nightly
The price is $579
Jan 12 - Jan 13, 2026
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
$387 nightly
The price is $442
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
Calverton
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
$574 nightly
The price is $656
Dec 27 - Dec 28
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

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.
$799 nightly
The price is $913
Jan 4 - Jan 5, 2026
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round

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.
$172 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Anchor at Soundview · Beach+Ocean+Sunrise

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.
$1,113 nightly
The price is $1,272
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

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.
$1,838 nightly
The price is $2,060
Jan 26 - Jan 27, 2026
Total with taxes and fees
Luxurious 3 BR Cottage w/ Ocean View Balcony

Beautifully farmhouse

Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
$1,028 nightly
The price is $1,175
Dec 29 - Dec 30
Total with taxes and fees
Beautifully farmhouse
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 $178 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 Sag Harbor Whaling and Historical Museum, 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.

How many vacation rentals are there in Sag Harbor?

With 309 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 Off the Rocker.

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.