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

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Our top choices for Sag Harbor holiday homes

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

A garden with hydrangea bushes, a stone wall, and a covered area with plants.

A modern living room with a sectional sofa, a chandelier, framed artwork, and a view through a glass door.

A wicker outdoor seating area with a dog on a cushioned bench.

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)

10/10

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!"

maria m.

The price is £842

£842

includes taxes & fees

1 Oct - 2 Oct

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.

A backyard with a swimming pool, outdoor furniture, and a fenced area.

A living room with a black sectional sofa, a white coffee table, a window with blinds, and an air conditioning unit.

A bedroom with a wooden floor, a bed with green and white striped bedding, a wicker side table, a wall-mounted air conditioner, and a window with blinds.

2. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool

Sag Harbor

The price is £1,645

£1,645

includes taxes & fees

5 Oct - 6 Oct

Lovely & Spacious Sag Harbor escape with heated pool

A driveway with a parked car, surrounded by trees and illuminated pathway lights.

A modern room with a bed, sofa, and a small table. There is a painting on the wall, a TV, and a lamp.

A residential driveway with a parked car, surrounded by greenery and a house.

A modern living room with a grey sofa, a round coffee table, and a painting of a pelican.

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)

10/10

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."

Robert R.

The price is £484

£484

includes taxes & fees

13 Oct - 14 Oct

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

A dining area with a round table, six chairs, and a chandelier.

A well-maintained lawn with a variety of trees and a small building, likely a house, surrounded by a fence.

A modern kitchen with white cabinets, a large island with bar stools, and a view of the outdoors.

A bedroom with a large bed, two bedside tables, a nightstand, and a window with curtains.

4. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home

East Hampton

9.2 out of 10, Wonderful, (7 reviews)

9.2/10

Wonderful

(7 reviews)

"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "

Suzanne R.

The price is £1,013

£1,013

includes taxes & fees

5 Oct - 6 Oct

Year round Jacuzzi - Blackberry Home

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

A two-story house with a balcony, a patio with outdoor furniture, and a fenced backyard.

A covered patio with outdoor furniture, a door, and a view of a residential area.

A sign welcoming visitors to the Greenport Visitors Dock with no commercial traffic.

5. The SandPiper

The SandPiper

Pipes Cove

9.6 out of 10, Exceptional, (52 reviews)

9.6/10

Exceptional

(52 reviews)

"Very wonderful location so close to the train station will come back soon"

Julian V.

The price is £242

£242

includes taxes & fees

18 Oct - 19 Oct

The SandPiper

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

A wicker lounge chair with a white cushion on a covered deck, surrounded by a white fence.

A modern kitchen with a washing machine, microwave, oven, and a ceiling fan.

A marina with several fishing boats docked.

6. Aqua Vista

Aqua Vista

Pipes Cove

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Great location and nice spot."

Kerri L.

The price is £242

£242

includes taxes & fees

7 Oct - 8 Oct

Aqua Vista

A rectangular swimming pool with a pebble border and a fire feature in the center.

A two-story house with a front porch, a brick chimney, and a well-maintained garden.

A spacious living area with a dark wooden floor, a white door with arched windows, a staircase, and a large painting on the wall.

A hallway with a bench, a fireplace, and a view of the living room.

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)

10/10

Exceptional

(1 review)

The price is £695

£695

includes taxes & fees

8 Oct - 9 Oct

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

An outdoor dining area with hanging lights, palm trees, and a bar.

A staircase with steps labeled 'STAIRWAY TO HEAVEN' leading to a room with a lamp and a plant.

A bar area with multiple bar stools, a counter with a variety of bottles and glasses, and pendant lighting.

A building with a porch, a tree, and a sign that reads "OPEN SPACE".

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)

9.4/10

Exceptional

(6 reviews)

"Great place! So nice."

Paul F.

The price is £235

£235

includes taxes & fees

4 Oct - 5 Oct

American Beech in Greenport - Petite King Room 7

A beach with people relaxing, a pier extending into the water, and a clear sky.

A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

A room with a sliding glass door leading to a garden, a small table, a chair, a television mounted on the wall, and a cabinet.

A two-story house with a front porch and a pathway leading to the entrance.

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)

10/10

Exceptional

(32 reviews)

"We had a great stay!! "

Callie E.

The price is £314

£314

includes taxes & fees

1 Oct - 2 Oct

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

A wooden pathway leading to a beach with scattered rocks and greenery.

A cozy room with a gray sofa, wooden walls, and large windows with blinds.

A spacious living room with a gray sofa, a wooden coffee table, and a dining area with a wooden table and chairs.

A modern kitchen with white cabinetry, a wooden door, and a long countertop.

10. Beach Block Hideaway

Beach Block Hideaway

Pipes Cove

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."

Teresa C.

The price is £382

£382

includes taxes & fees

4 Oct - 5 Oct

Beach Block Hideaway

An outdoor seating area with umbrellas and wooden furniture, overlooking a body of water.

A bedroom with a bed, bench, and a window with a view.

A kitchen with white cabinetry, a wooden dining table, and chairs. There is a window with a view of trees.

A kitchen with a wooden chair, a cabinet with glass doors, and a wall-mounted lamp.

11. Huge Island Getaway Pool Hot Tub Walk To Beach

Huge Island Getaway Pool Hot Tub Walk To Beach

Menantic Creek

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"Property great. Beautiful home with great amenities"

Harry K.

The price is £843

£843

includes taxes & fees

5 Oct - 6 Oct

Huge Island Getaway Pool Hot Tub Walk To Beach

A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

A modern living room with a sectional sofa, a glass coffee table, and large windows offering a view of greenery outside.

A backyard with a swimming pool, lounge chairs, and umbrellas.

A modern bathroom with a large arched window, a white bathtub, a white chair, and a bed.

12. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island

10.0 out of 10, Exceptional, (59 reviews)

10/10

Exceptional

(59 reviews)

"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"

Kathleen Andrews K.

Work and Play Special! Extended Stay Discount

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

A rectangular swimming pool with a brick border, surrounded by lush green trees and a brick patio with white lounge chairs.

A spacious living room with a sofa, armchairs, a coffee table, and a large window with a view of trees.

A modern kitchen with white cabinets, a dining table with white chairs, and a staircase with a metal railing.

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, (2 reviews)

10/10

Exceptional

(2 reviews)

"Great clean beautiful property."

ANGELA S.

The price is £803

£803

includes taxes & fees

19 Oct - 20 Oct

Spacious house in East Hampton with heated pool + WFH

A kitchen with a central island, white cabinetry, and a brick accent wall.

An outdoor dining area with a brick fireplace, a table set for four, and a white door in the background.

A spacious living room with a white fireplace, a large mirror, and a view of the outdoors.

A spacious living room with a white sofa, a coffee table, and a dining area with a table and chairs.

14. !! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

Wainscott

10.0 out of 10, Exceptional, (33 reviews)

10/10

Exceptional

(33 reviews)

"Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend! "

Leigh E.

The price is £1,693

£1,693

includes taxes & fees

13 Oct - 14 Oct

!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

A modern kitchen with a central island, white cabinetry, and a view to the dining area.

A spacious living room with a fireplace, two sofas, a coffee table, and a TV.

A spacious living room with a white sofa, a coffee table, and a blue patterned rug. There is a staircase leading to an upper level, and a bookshelf filled with books and decorative items.

15. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool

Southampton

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Very cozy house in a great location!"

Serina R.

The price is £1,219

£1,219

includes taxes & fees

26 Oct - 27 Oct

Amazing Southampton Home with Private Heated Pool

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

A bedroom with a large bed, a TV mounted on the wall, and a desk with a chair.

A wooden patio with a table and chairs, an umbrella, and a white fence.

A modern kitchen with white cabinets, a central island, and a built-in oven.

16. 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)

10/10

Exceptional

(6 reviews)

"perfect for families"

Okito H.

The price is £832

£832

includes taxes & fees

1 Oct - 2 Oct

Minutes from the beach, brand new 4 bedroom

A modern dining area with a wooden table, white chairs, and a chandelier.

A bedroom with a bed, a small side table with a plant, and a window with blinds.

A living room with a grey sofa, a round coffee table with magazines, a wooden side table, and a large mirror on the wall.

A staircase with a black handrail and balusters, a white wall, a fireplace with a TV above it, and a door to the right.

17. Northfork Townhouse walk to all

Northfork Townhouse walk to all

Greenport

9.4 out of 10, Exceptional, (8 reviews)

9.4/10

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"

Beth R.

The price is £534

£534

includes taxes & fees

20 Oct - 21 Oct

Northfork Townhouse walk to all

A modern building with large windows overlooking a beach.

A modern kitchen with white cabinets and a built-in oven.

A modern kitchen with a view of the sea, large windows, and a sliding glass door to the outdoors.

A modern bedroom with a large bed, a wardrobe, a mirror, and a view of the sea.

18. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

9.4 out of 10, Exceptional, (20 reviews)

9.4/10

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."

Donald J.

The price is £953

£953

includes taxes & fees

13 Oct - 14 Oct

Beachfront Jacuzzi All Year - Black Swan Home

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

A spacious living room with two white armchairs, a wooden coffee table, and a stone wall.

A sandy beach with waves, a clear sky, and a few people.

A narrow hallway with a bed and a TV in the background.

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)

9.2/10

Wonderful

(11 reviews)

"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"

Justin

The price is £724

£724

includes taxes & fees

21 Oct - 22 Oct

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

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.

A modern kitchen with white cabinetry, stainless steel appliances, and a herringbone-patterned backsplash.

A bedroom with a bed, a bench, a chandelier, and a wall-mounted mirror.

A modern kitchen with a marble island, pendant lights, and a patterned backsplash.

20. Renovated Townhouse walk to all

Renovated Townhouse walk to all

Greenport

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"The place was as advertised and in great walking distance to everything in town! "

Liz H.

The price is £497

£497

includes taxes & fees

29 Oct - 30 Oct

Renovated Townhouse walk to all

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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