The 25 Best Vacation-Home Small Towns in New York

Ranked on The Town Files lifestyle rankings among 707 towns of 500–10,000 people in New York. #1 is Montauk, NY.

1. 25Water Mill, New York

   Better for a vacation home than 96% of New York towns

   Water Mill is a community of 2,506 people in Suffolk County, New York. It also ranks more seaside character than 95% of New York towns and more upscale than 94% of New York towns.

   2,506 people · Suffolk County · median home $2,000,001 · income $186,875 · Jan low 23°F · 27 in snow

   Full Water Mill, New York profile: weather, storms, schools, jobs →

2. 24Berne, New York

   Better for a vacation home than 96% of New York towns

   Berne is a town of 2,689 people in Albany County, New York. It also ranks easier by car than 98% of New York towns and quieter than 93% of New York towns.

   2,689 people · Albany County · median home $296,300 · income $105,219 · Jan low 13°F · 53 in snow

   Full Berne, New York profile: weather, storms, schools, jobs →

3. 23Bridgehampton, New York

   Better for a vacation home than 96% of New York towns

   Bridgehampton is a community of 2,953 people in Suffolk County, New York. It also ranks more seaside character than 95% of New York towns and more upscale than 89% of New York towns.

   2,953 people · Suffolk County · median home $1,764,800 · income $139,486 · Jan low 23°F · 27 in snow

   Full Bridgehampton, New York profile: weather, storms, schools, jobs →

4. 22Southampton, New York

   Better for a vacation home than 96% of New York towns

   Southampton is a village of 4,550 people in Suffolk County, New York. It also ranks more upscale than 95% of New York towns and better transit than 95% of New York towns.

   4,550 people · Suffolk County · median home $2,000,001 · income $214,032 · Jan low 23°F · 27 in snow

   Full Southampton, New York profile: weather, storms, schools, jobs →

5. 21East Hampton North, New York

   Better for a vacation home than 96% of New York towns

   East Hampton North is a community of 5,377 people in Suffolk County, New York. It also ranks hipper than 75% of New York towns and better transit than 71% of New York towns.

   5,377 people · Suffolk County · median home $1,077,000 · income $109,035 · Jan low 23°F · 27 in snow

   Full East Hampton North, New York profile: weather, storms, schools, jobs →

6. 20Cape Vincent, New York

   Better for a vacation home than 97% of New York towns

   Cape Vincent is a town of 2,765 people in Jefferson County, New York. It also ranks more of a college town than 89% of New York towns and better for retirees than 82% of New York towns.

   2,765 people · Jefferson County · median home $238,700 · income $61,402 · Jan low 10°F · 116 in snow

   Full Cape Vincent, New York profile: weather, storms, schools, jobs →

7. 19Shandaken, New York

   Better for a vacation home than 97% of New York towns

   Shandaken is a town of 2,866 people in Ulster County, New York. It also ranks hipper than 99% of New York towns and quieter than 98% of New York towns.

   2,866 people · Ulster County · median home $346,100 · income $66,031 · Jan low 12°F · 105 in snow

   Full Shandaken, New York profile: weather, storms, schools, jobs →

8. 18Otsego, New York

   Better for a vacation home than 97% of New York towns

   Otsego is a town of 3,641 people in Otsego County, New York. It also ranks better for retirees than 99% of New York towns and hipper than 96% of New York towns.

   3,641 people · Otsego County · median home $352,600 · income $72,891 · Jan low 14°F · 86 in snow

   Full Otsego, New York profile: weather, storms, schools, jobs →

9. 17Southold, New York

   Better for a vacation home than 97% of New York towns

   Southold is a community of 6,040 people in Suffolk County, New York. It also ranks more seaside character than 96% of New York towns and better for retirees than 88% of New York towns.

   6,040 people · Suffolk County · median home $844,700 · income $128,822 · Jan low 23°F · 27 in snow

   Full Southold, New York profile: weather, storms, schools, jobs →

10. 16Remsenburg-Speonk, New York

    Better for a vacation home than 98% of New York towns

    Remsenburg-Speonk is a community of 3,110 people in Suffolk County, New York. It also ranks more seaside character than 94% of New York towns and better for retirees than 93% of New York towns.

    3,110 people · Suffolk County · median home $998,000 · income $169,091 · Jan low 20°F · 30 in snow

    Full Remsenburg-Speonk, New York profile: weather, storms, schools, jobs →

11. 15Galway, New York

    Better for a vacation home than 98% of New York towns

    Galway is a town of 3,525 people in Saratoga County, New York. It also ranks better for families than 97% of New York towns and more of a college town than 95% of New York towns.

    3,525 people · Saratoga County · median home $365,100 · income $110,149 · Jan low 14°F · 62 in snow

    Full Galway, New York profile: weather, storms, schools, jobs →

12. 14Hamilton, New York

    Better for a vacation home than 98% of New York towns

    

    Hamilton is a village of 4,107 people in Madison County, New York. It also ranks better for young professionals than 100% of New York towns and hipper than 99% of New York towns.

    4,107 people · Madison County · median home $264,200 · income $66,750 · Jan low 11°F · 77 in snow

    Full Hamilton, New York profile: weather, storms, schools, jobs →

13. 13Olive, New York

    Better for a vacation home than 98% of New York towns

    Olive is a town of 4,226 people in Ulster County, New York. It also ranks better for retirees than 97% of New York towns and quieter than 87% of New York towns.

    4,226 people · Ulster County · median home $375,100 · income $114,018 · Jan low 12°F · 105 in snow

    Full Olive, New York profile: weather, storms, schools, jobs →

14. 12Mattituck, New York

    Better for a vacation home than 98% of New York towns

    Mattituck is a community of 4,322 people in Suffolk County, New York. It also ranks more seaside character than 96% of New York towns and better for families than 92% of New York towns.

    4,322 people · Suffolk County · median home $750,000 · income $121,250 · Jan low 23°F · 27 in snow

    Full Mattituck, New York profile: weather, storms, schools, jobs →

15. 11Noyack, New York

    Better for a vacation home than 98% of New York towns

    Noyack is a community of 4,325 people in Suffolk County, New York. It also ranks more seaside character than 95% of New York towns and better for families than 92% of New York towns.

    4,325 people · Suffolk County · median home $1,085,500 · income $118,728 · Jan low 23°F · 27 in snow

    Full Noyack, New York profile: weather, storms, schools, jobs →

16. 10Springs, New York

    Better for a vacation home than 98% of New York towns

    Springs is a community of 8,086 people in Suffolk County, New York. It also ranks more seaside character than 95% of New York towns and more upscale than 86% of New York towns.

    8,086 people · Suffolk County · median home $948,500 · income $144,836 · Jan low 23°F · 27 in snow

    Full Springs, New York profile: weather, storms, schools, jobs →

17. 9Woodstock, New York

    Better for a vacation home than 99% of New York towns

    Woodstock is a community of 2,521 people in Ulster County, New York. It also ranks better for retirees than 100% of New York towns and hipper than 99% of New York towns.

    2,521 people · Ulster County · median home $675,600 · income $52,091 · Jan low 12°F · 86 in snow

    Full Woodstock, New York profile: weather, storms, schools, jobs →

18. 8Shelter Island, New York

    Better for a vacation home than 99% of New York towns

    

    Shelter Island is a town of 3,253 people in Suffolk County, New York. It also ranks more seaside character than 96% of New York towns and better for retirees than 95% of New York towns.

    3,253 people · Suffolk County · median home $1,104,300 · income $133,967 · Jan low 23°F · 27 in snow

    Full Shelter Island, New York profile: weather, storms, schools, jobs →

19. 7Cutchogue, New York

    Better for a vacation home than 99% of New York towns

    Cutchogue is a community of 3,437 people in Suffolk County, New York. It also ranks better for retirees than 98% of New York towns and more seaside character than 97% of New York towns.

    3,437 people · Suffolk County · median home $917,800 · income $143,472 · Jan low 23°F · 27 in snow

    Full Cutchogue, New York profile: weather, storms, schools, jobs →

20. 6Northwest Harbor, New York

    Better for a vacation home than 99% of New York towns

    Northwest Harbor is a community of 4,637 people in Suffolk County, New York. It also ranks better for retirees than 98% of New York towns and more seaside character than 95% of New York towns.

    4,637 people · Suffolk County · median home $1,573,300 · income $160,375 · Jan low 23°F · 27 in snow

    Full Northwest Harbor, New York profile: weather, storms, schools, jobs →

21. 5East Quogue, New York

    Better for a vacation home than 99% of New York towns

    East Quogue is a community of 5,557 people in Suffolk County, New York. It also ranks more seaside character than 94% of New York towns and better for retirees than 90% of New York towns.

    5,557 people · Suffolk County · median home $844,100 · income $93,710 · Jan low 20°F · 27 in snow

    Full East Quogue, New York profile: weather, storms, schools, jobs →

22. 4Woodstock, New York

    Better for a vacation home than 99% of New York towns

    Woodstock is a town of 6,287 people in Ulster County, New York. It also ranks better for retirees than 100% of New York towns and hipper than 99% of New York towns.

    6,287 people · Ulster County · median home $604,700 · income $92,118 · Jan low 12°F · 86 in snow

    Full Woodstock, New York profile: weather, storms, schools, jobs →

23. 3Sag Harbor, New York

    Better for a vacation home than 100% of New York towns

    Sag Harbor is a village of 2,772 people in Suffolk County, New York. It also ranks better for retirees than 99% of New York towns and more seaside character than 96% of New York towns.

    2,772 people · Suffolk County · median home $1,615,900 · income $129,821 · Jan low 23°F · 27 in snow

    Full Sag Harbor, New York profile: weather, storms, schools, jobs →

24. 2Westhampton, New York

    Better for a vacation home than 100% of New York towns

    Westhampton is a community of 3,621 people in Suffolk County, New York. It also ranks more seaside character than 94% of New York towns and better for families than 92% of New York towns.

    3,621 people · Suffolk County · median home $1,018,200 · income $119,886 · Jan low 20°F · 29 in snow

    Full Westhampton, New York profile: weather, storms, schools, jobs →

25. 1Montauk, New York

    Better for a vacation home than 100% of New York towns

    Montauk is a community of 4,318 people in Suffolk County, New York. It also ranks more seaside character than 95% of New York towns and better for retirees than 94% of New York towns.

    4,318 people · Suffolk County · median home $1,356,600 · income $142,961 · Jan low 28°F · 26 in snow

    Full Montauk, New York profile: weather, storms, schools, jobs →

Price vs ranking

More New York rankings

• The 25 Best Small Towns to Retire in New York
• The 25 Quietest Small Towns in New York
• The 25 Most Affordable Small Towns in New York
• The 25 Best Small Towns for Families in New York
• The 25 Best Quiet, Affordable Small Towns to Retire in New York
• 25 Small Towns in New York With the Cheapest Homes
• 25 Small Towns in New York With the Mildest Winters
• The 25 Most Walkable Small Towns in New York
• 25 Small Towns in New York With the Fewest Tornadoes Since 1950
• The 25 Best Small Towns for First-Time Home Buyers in New York

Same ranking, other places

• The 50 Best Vacation-Home Small Towns in America
• The 25 Best Vacation-Home Small Towns in Pennsylvania
• The 25 Best Vacation-Home Small Towns in Michigan
• The 25 Best Vacation-Home Small Towns in Texas
• The 25 Best Vacation-Home Small Towns in California
• The 25 Best Vacation-Home Small Towns in New Jersey