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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 ￥89,535
￥175,904 total
includes taxes & fees
Oct 7 - Oct 8
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 ￥241,602
￥351,443 total
includes taxes & fees
Oct 7 - Oct 8
Lovely & Spacious Sag Harbor escape with heated pool
A dining area with a round table, six chairs, and a chandelier.

3. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton 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 ￥13,896
￥203,814 total
includes taxes & fees
Oct 7 - Oct 8
Year round Jacuzzi - Blackberry East Hampton Home
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

4. 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 ￥45,004
￥92,732 total
includes taxes & fees
Nov 1 - Nov 2
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
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, (54 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 4 - Nov 5
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, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,897
￥50,517 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.

7. 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, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥22,888
￥60,597 total
includes taxes & fees
Nov 5 - Nov 6
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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
￥47,972 total
includes taxes & fees
Nov 5 - Nov 6
American Beech in Greenport - Petite King Room 7
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

9. 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 ￥24,871
￥91,741 total
includes taxes & fees
Oct 7 - Oct 8
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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 ￥30,792
￥71,081 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 ￥71,060
￥167,968 total
includes taxes & fees
Oct 19 - Oct 20
Spacious house in East Hampton with heated pool + WFH
A modern building with large windows overlooking a beach.

12. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 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
￥190,187 total
includes taxes & fees
Oct 14 - Oct 15
Beachfront Jacuzzi All Year - Black Swan Home
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

13. 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 ￥107,379
￥215,663 total
includes taxes & fees
Oct 21 - Oct 22
Amazing Southampton Home with Private Heated Pool
A modern dining area with a wooden table, white chairs, and a chandelier.

14. 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 ￥41,925
￥91,919 total
includes taxes & fees
Nov 2 - Nov 3
Northfork Townhouse walk to all
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 ￥71,060
￥175,181 total
includes taxes & fees
Oct 7 - Oct 8
Minutes from the beach, brand new 4 bedroom
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.

16. 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 ￥46,189
￥97,514 total
includes taxes & fees
Nov 2 - Nov 3
Renovated Townhouse walk to all
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

17. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.0 out of 10, Very good, (2 reviews)
"Great location a few steps always from the ocean and a few minutes away from town"
United States
Jessica S.
The price is ￥47,689
￥97,157 total
includes taxes & fees
Oct 12 - Oct 13
Unit 1311: Cottage | Garden View | Deuce
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

18. 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 ￥17,686
￥263,077 total
includes taxes & fees
Oct 12 - Oct 13
Jacuzzi year-round - Villa Luz Private Home
A wooden house with a front porch, white railings, and a double door.

19. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is ￥337,580
￥456,311 total
includes taxes & fees
Oct 7 - Oct 8
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
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 ￥36,161
￥54,485 total
includes taxes & fees
Oct 12 - Oct 13
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Great"
Dillon 1-night trip
Posted 1 hour ago
Offshore Montauk

Find out more about Sag Harbor

Sag Harbor Vacation Homes information

Number of reviews
231
Accommodation
1192 Vacation Homes
Lowest Price
￥39,676
Highest Price
￥456,311