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

Holiday Homes in Sag Harbor

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Sag Harbor holiday homes

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

1. 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 AU$1,992
includes taxes & fees
2 Sept - 3 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

2. 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, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is AU$802
includes taxes & fees
21 Sept - 22 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A wooden pathway leading to a beach with scattered rocks and greenery.

3. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AU$566
includes taxes & fees
7 Sept - 8 Sept
Beach Block Hideaway
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is AU$484
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
A beach with people relaxing, a pier extending into the water, and a clear sky.

5. 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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$573
includes taxes & fees
15 Sept - 16 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

6. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$519
includes taxes & fees
15 Sept - 16 Sept
Aqua Vista
A modern living room with a fireplace, a sofa, a chair, and a coffee table.

7. Beautiful East Hampton Retreat

Beautiful East Hampton Retreat
East Hampton
9.6 out of 10, Exceptional, (5 reviews)
"The host was very easy to work with. He was attentive and responsive. The home was exactly as advertised and was clean and nice to stay in!"
United States
Jonathan S.
The price is AU$1,890
includes taxes & fees
2 Sept - 3 Sept
Beautiful East Hampton Retreat
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

8. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is AU$1,806
includes taxes & fees
15 Sept - 16 Sept
Work and Play Special! Extended Stay Discount
An outdoor dining area with hanging lights, palm trees, and a bar.

9. 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 AU$592
includes taxes & fees
2 Sept - 3 Sept
American Beech in Greenport - Petite King Room 7
A dining area with a round table, six chairs, and a chandelier.

10. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"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 AU$2,285
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong
A rectangular swimming pool with a pebble border and a fire feature in the center.

11. Amagansett Farmhouse Retreat - Heated Pool, Outdoor Fireplace & Basement Arcade, Great for Kids

Amagansett Farmhouse Retreat - Heated Pool, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
The price is AU$1,836
includes taxes & fees
7 Sept - 8 Sept
Amagansett Farmhouse Retreat - Heated Pool, Outdoor Fireplace & Basement Arcade, Great for Kids
A spacious room with a wooden dining table, white chairs, and a large window providing a view of the outdoors.

12. Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool

Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool
East Hampton North
The price is AU$1,921
includes taxes & fees
28 Sept - 29 Sept
Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

13. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Great clean beautiful property."
United States
ANGELA S.
The price is AU$1,616
includes taxes & fees
27 Sept - 28 Sept
Spacious house in East Hampton with heated pool + WFH
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

14. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is AU$1,537
includes taxes & fees
15 Sept - 16 Sept
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

15. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is AU$1,823
includes taxes & fees
7 Sept - 8 Sept
Minutes from the beach, brand new 4 bedroom
A modern dining area with a wooden table, white chairs, and a chandelier.

16. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (7 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is AU$1,275
includes taxes & fees
17 Sept - 18 Sept
Northfork Townhouse walk to all
A stone pier leading to a beach with houses in the background.

17. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is AU$418
includes taxes & fees
30 Sept - 1 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

18. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (13 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is AU$1,055
includes taxes & fees
17 Sept - 18 Sept
Renovated Townhouse walk to all
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

19. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is AU$1,331
includes taxes & fees
8 Sept - 9 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
A sandy beach with footprints leading to the water, a wooden bench, and a pair of shoes on the ground.

20. Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is AU$1,247
includes taxes & fees
20 Sept - 21 Sept
Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes from the downtown area. Highly recommend this property."
Arabella 1-night trip
Posted 11 hours ago
Montauk Yacht Club

Find out more about Sag Harbor

Sag Harbor Holiday Homes information

Number of reviews
342
Accommodation
1363 Holiday Homes
Lowest Price
AU$418
Highest Price
AU$2,285