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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Sag Harbor vacation 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 ￥89,501
￥175,837 total
includes taxes & fees
Oct 6 - Oct 7
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

2. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is ￥241,511
￥351,130 total
includes taxes & fees
Oct 5 - Oct 6
Lovely & Spacious Sag Harbor escape with heated pool
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

3. 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 ￥44,987
￥92,697 total
includes taxes & fees
Nov 1 - Nov 2
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A dining area with a round table, six chairs, and a chandelier.

4. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home
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 ￥17,837
￥208,615 total
includes taxes & fees
Oct 4 - Oct 5
Year round Jacuzzi - Blackberry Home
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥14,996
￥39,676 total
includes taxes & fees
Nov 2 - Nov 3
The SandPiper
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, (48 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,888
￥50,498 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
A rectangular swimming pool with a pebble border and a fire feature in the center.

7. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
10.0 out of 10, Exceptional, (1 review)
The price is ￥37,846
￥150,887 total
includes taxes & fees
Oct 8 - Oct 9
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
An outdoor dining area with hanging lights, palm trees, and a bar.

8. 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 ￥31,412
￥48,334 total
includes taxes & fees
Oct 4 - Oct 5
American Beech in Greenport - Petite King Room 7
A beach with people relaxing, a pier extending into the water, and a clear sky.

9. 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, (32 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥22,888
￥60,597 total
includes taxes & fees
Nov 1 - Nov 2
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden pathway leading to a beach with scattered rocks and greenery.

10. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥30,781
￥70,875 total
includes taxes & fees
Nov 3 - Nov 4
Beach Block Hideaway
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

11. 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, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is ￥71,033
￥164,657 total
includes taxes & fees
Oct 19 - Oct 20
Spacious house in East Hampton with heated pool + WFH
A kitchen with a central island, white cabinetry, and a brick accent wall.

12. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (33 reviews)
"Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend! "
United States
Leigh E.
The price is ￥166,500
￥361,011 total
includes taxes & fees
Oct 4 - Oct 5
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
A modern building with large windows overlooking a beach.

13. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is ￥22,257
￥194,695 total
includes taxes & fees
Oct 4 - Oct 5
Beachfront Jacuzzi All Year - Black Swan Home
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

14. 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 ￥71,033
￥175,115 total
includes taxes & fees
Oct 6 - Oct 7
Minutes from the beach, brand new 4 bedroom
A modern dining area with a wooden table, white chairs, and a chandelier.

15. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 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 ￥52,624
￥105,080 total
includes taxes & fees
Oct 20 - Oct 21
Northfork Townhouse walk to all
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

16. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥17,679
￥264,960 total
includes taxes & fees
Oct 8 - Oct 9
Jacuzzi year-round - Villa Luz Private Home
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

17. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is ￥106,864
￥215,402 total
includes taxes & fees
Oct 20 - Oct 21
Amazing Southampton Home with Private Heated Pool
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
9.6 out of 10, Exceptional, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is ￥50,491
￥103,004 total
includes taxes & fees
Oct 26 - Oct 27
Renovated Townhouse walk to all
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

19. 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 ￥55,405
￥132,193 total
includes taxes & fees
Oct 6 - Oct 7
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

20. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is ￥36,148
￥54,465 total
includes taxes & fees
Oct 6 - Oct 7
American Beech in Greenport - Deluxe King 6
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The property was definitely worth a five-star rating and the views of the Bay were tremendous! The rooms were very clean and the beds were super comfortable. I had a wonderful breakfast looking out over the water. It was magical"
Melanie 1-night trip
Posted 10 hours ago
Water's Edge Resort & Spa

Find out more about Sag Harbor

Sag Harbor Vacation Homes information

Number of reviews
233
Accommodation
1002 Vacation Homes
Lowest Price
￥39,676
Highest Price
￥361,011