Sag Harbor Vacation Homes

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.

1. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

maria m.

HK$8,825 total

includes taxes & fees

29 Oct - 30 Oct

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

Sag Harbor

HK$17,289 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

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

Bridgehampton

Katie B.

HK$4,607 total

includes taxes & fees

8 Nov - 9 Nov

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

4. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

HK$11,467 total

includes taxes & fees

8 Nov - 9 Nov

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

5. The SandPiper

Pipes Cove

Manuela C.

HK$1,905 total

includes taxes & fees

10 Nov - 11 Nov

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

6. Aqua Vista

Pipes Cove

Kerri L.

HK$1,999 total

includes taxes & fees

9 Nov - 10 Nov

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

Pipes Cove

Callie E.

HK$2,872 total

includes taxes & fees

5 Nov - 6 Nov

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

8. Beach Block Hideaway

Pipes Cove

Teresa C.

HK$3,531 total

includes taxes & fees

3 Nov - 4 Nov

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

9. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

HK$2,402 total

includes taxes & fees

29 Oct - 30 Oct

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

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

Southampton

Justin

HK$5,064 total

includes taxes & fees

11 Nov - 12 Nov

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

East Hampton

ANGELA S.

HK$10,776 total

includes taxes & fees

5 Nov - 6 Nov

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

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

Wainscott

Suzanne B.

HK$17,927 total

includes taxes & fees

12 Nov - 13 Nov

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

13. Northfork Townhouse walk to all

Greenport

Beth R.

HK$4,517 total

includes taxes & fees

11 Nov - 12 Nov

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.

14. Renovated Townhouse walk to all

Greenport

Liz H.

HK$4,428 total

includes taxes & fees

12 Nov - 13 Nov

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

15. Amazing Southampton Home with Private Heated Pool

Southampton

Serina R.

HK$9,888 total

includes taxes & fees

29 Oct - 30 Oct

A modern bathroom with a glass shower enclosure, a toilet with a paper towel dispenser, and a sign advising against flushing paper towels.

16. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

HK$14,479 total

includes taxes & fees

29 Oct - 30 Oct

A modern building with large windows overlooking a beach.

17. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

HK$10,625 total

includes taxes & fees

1 Nov - 2 Nov

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

18. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

HK$8,703 total

includes taxes & fees

1 Nov - 2 Nov

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...

Southampton

Melissa

HK$22,668 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a sofa, armchairs, a coffee table, and a TV.

20. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

HK$9,213 total

includes taxes & fees

3 Nov - 4 Nov

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Top Sag Harbor Hotel Reviews

Saybrook Point Resort & Marina

10/10 Excellent

"Our room was beautiful and unique. Balcony with a water view. The pools were heated perfectly. The patio pool was perfect, we ven on a 60 degree day"

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

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