The 25 Best Vacation-Home Small Towns in New York

Ranked on The Town Files lifestyle rankings among 707 towns of 2,500–10,000 people in New York. #1 is Montauk, NY.

1. 25Water Mill, New York

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

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

2. 24Berne, New York

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

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

3. 23Bridgehampton, New York

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

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

4. 22Southampton, New York

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

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

5. 21East Hampton North, New York

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

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

6. 20Cape Vincent, New York

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

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

7. 19Shandaken, New York

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

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

8. 18Otsego, New York

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

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

9. 17Southold, New York

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

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

10. 16Remsenburg-Speonk, New York

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

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

11. 15Galway, New York

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

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

12. 14Hamilton, New York

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

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

13. 13Olive, New York

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

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

14. 12Mattituck, New York

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

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

15. 11Noyack, New York

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

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

16. 10Springs, New York

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

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

17. 9Woodstock, New York

    Better for a vacation home 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

18. 8Shelter Island, New York

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

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

19. 7Cutchogue, New York

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

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

20. 6Northwest Harbor, New York

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

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

21. 5East Quogue, New York

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

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

22. 4Woodstock, New York

    Better for a vacation home 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

23. 3Sag Harbor, New York

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

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

24. 2Westhampton, New York

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

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

25. 1Montauk, New York

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

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

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