Sag Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Sag Harbor vacation rentals

Beach
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.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is ￥624,480
￥1,017,584 total
includes taxes & fees
Dec 29 - Dec 30
Spacious 5-bedroom house with water views and 2 houses from the bay.
5 bedrooms, iron/ironing board, WiFi, bed sheets
Sag Harbor Water View w Dock 1.5ml from town

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 ￥702,540
￥998,144 total
includes taxes & fees
Dec 27 - Dec 28
Sag Harbor Water View w Dock 1.5ml from town
Front of property - evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1271)
"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 ￥21,638
￥27,777 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Montauk Manor
Beach
Seabreeze #4: Charming Cottage Footsteps to the Beach

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.
The price is ￥8,587
￥69,741 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Seabreeze #4: Charming Cottage Footsteps to the Beach
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

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 ￥12,073
￥30,417 total
includes taxes & fees
Jan 3 - Jan 4, 2026
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
The price is ￥13,489
￥29,227 total
includes taxes & fees
Jan 6 - Jan 7, 2026
1-bedroom cottage with Grove Beach 🏖️ access.
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

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 ￥23,418
￥198,703 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
Offshore Residences

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is ￥74,781
￥103,272 total
includes taxes & fees
Dec 29 - Dec 30
Offshore Residences
TV, table tennis
My Humble Abode 2BR Beachside Home | TennisPoolPKG

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 ￥139,415
￥235,988 total
includes taxes & fees
Jan 15 - Jan 16, 2026
My Humble Abode 2BR Beachside Home | TennisPoolPKG
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

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 ￥23,699
￥81,310 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beachside Bliss w/ Game Room, Gym & Golf Green
A heated pool
Your Quietude 1BR Beachside Home |Tennis+Pool+WiFi

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
The price is ￥71,035
￥134,502 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Your Quietude 1BR Beachside Home |Tennis+Pool+WiFi
Fridge, microwave, stovetop, dishwasher
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

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 ￥42,933
￥90,790 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

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.
The price is ￥39,030
￥90,315 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Smart TV
Seabreeze #3: Cozy Cottage by the beach

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 ￥8,587
￥69,029 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Seabreeze #3: Cozy Cottage by the beach
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

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.
The price is ￥48,202
￥103,765 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

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 ￥15,456
￥142,517 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Blackberry: Private home with jacuzzi year-round
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

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 ￥12,073
￥30,417 total
includes taxes & fees
Jan 3 - Jan 4, 2026
The Anchor at Soundview · Beach+Ocean+Sunrise
Terrace/patio
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

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 ￥15,456
￥198,522 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
A heated pool
Luxurious 3 BR Cottage w/ Ocean View Balcony

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 ￥200,926
￥327,316 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Luxurious 3 BR Cottage w/ Ocean View Balcony
Terrace/patio
Beautifully farmhouse

Beautifully farmhouse

Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
The price is ￥93,672
￥183,363 total
includes taxes & fees
Dec 25 - Dec 26
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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Room was beautiful and spacious. Staff was courteous and on point. "
Ron 2-night trip
Posted 2 days ago
The Bentley Hotel Southampton

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 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.

What are some of the best vacation home rentals that Sag Harbor has to offer?

Escape to Sag Harbor: This Sag Harbor vacation home rental offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 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 patio, a garden, and a pool table so you can immerse yourself in your vacation. Our travelers also rate 9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub as a favorite home for rent in Sag Harbor.

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.