The Town Files

The 50 Best Vacation-Home Small Towns in America

Ranked on The Town Files lifestyle rankings among 7,696 towns of 2,500–10,000 people in the U.S.. #1 is Pelican Bay, FL.

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Numbers match the ranking.
The 50 Best Vacation-Home Small Towns in America1. Pelican Bay, FL100th pct2. Chatham, MA100th pct3. Woodstock, NY100th pct4. Eastham, MA100th pct5. Jamestown, RI100th pct6. Rye, NH100th pct7. Camden, ME100th pct8. Bar Harbor, ME100th pct9. Butler Beach, FL100th pct10. Northwest Harbor, NY100th pct11. Montauk, NY100th pct12. Highland Beach, FL100th pct13. Indian River Shores, FL100th pct14. Beach Haven West, NJ100th pct15. Vineyards, FL100th pct16. Camden, ME100th pct17. South Beach, FL100th pct18. Essex, MA100th pct19. Westhampton, NY100th pct20. Little Compton, RI100th pct21. Big Sky, MT100th pct22. Wellfleet, MA100th pct23. West Tisbury, MA100th pct24. Grantham, NH100th pct25. Ponce Inlet, FL100th pct
  1. 50Siesta Key, Florida

    Better for a vacation home than 99% of U.S. towns

    5,454 people · Sarasota County · median home $985,800 · income $115,854 · Jan low 52°F · 0 in snow

  2. 49East Quogue, New York

    Better for a vacation home than 99% of U.S. towns

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

  3. 48Village of Oak Creek (Big Park), Arizona

    Better for a vacation home than 99% of U.S. towns

    6,128 people · Yavapai County · median home $741,100 · income $80,878 · Jan low 34°F · 26 in snow

  4. 47Orleans, Massachusetts

    Better for a vacation home than 99% of U.S. towns

    6,307 people · Barnstable County · median home $957,000 · income $102,335 · Jan low 26°F · 25 in snow

  5. 46Mattapoisett, Massachusetts

    Better for a vacation home than 99% of U.S. towns

    6,508 people · Plymouth County · median home $681,600 · income $130,241 · Jan low 22°F · 33 in snow

  6. 45Snyderville, Utah

    Better for a vacation home than 99% of U.S. towns

    6,744 people · Summit County · median home $1,104,200 · income $143,517 · Jan low 16°F · 153 in snow

  7. 44St. Augustine Beach, Florida

    Better for a vacation home than 99% of U.S. towns

    6,803 people · St. Johns County · median home $634,400 · income $100,802 · Jan low 48°F · 0 in snow

  8. 43Longboat Key, Florida

    Better for a vacation home than 99% of U.S. towns

    7,505 people · Sarasota County · median home $1,022,100 · income $158,030 · Jan low 52°F · 0 in snow

  9. 42Brigantine, New Jersey

    Better for a vacation home than 99% of U.S. towns

    7,716 people · Atlantic County · median home $524,800 · income $97,250 · Jan low 30°F · 15 in snow

  10. 41Charlestown, Rhode Island

    Better for a vacation home than 99% of U.S. towns

    7,997 people · Washington County · median home $525,500 · income $109,404 · Jan low 25°F · 32 in snow

  11. 40Springs, New York

    Better for a vacation home than 99% of U.S. towns

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

  12. 39Vilano Beach, Florida

    Better for a vacation home than 100% of U.S. towns

    2,514 people · St. Johns County · median home $648,900 · income $120,750 · Jan low 48°F · 0 in snow

  13. 38Ferrisburgh, Vermont

    Better for a vacation home than 100% of U.S. towns

    2,646 people · Addison County · median home $422,700 · income $106,989 · Jan low 9°F · 79 in snow

  14. 37Thornton, New Hampshire

    Better for a vacation home than 100% of U.S. towns

    2,708 people · Grafton County · median home $351,900 · income $90,022 · Jan low 6°F · 70 in snow

  15. 36Pepperdine University, California

    Better for a vacation home than 100% of U.S. towns

    2,747 people · Los Angeles County · median home $979,700 · income $199,432 · Jan low 50°F · 0 in snow

  16. 35Sag Harbor, New York

    Better for a vacation home than 100% of U.S. towns

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

  17. 34Spring Lake, New Jersey

    Better for a vacation home than 100% of U.S. towns

    2,789 people · Monmouth County · median home $2,000,001 · income $215,625 · Jan low 25°F

  18. 33Island Walk, Florida

    Better for a vacation home than 100% of U.S. towns

    2,812 people · Collier County · median home $667,900 · income $81,103 · Jan low 52°F · 0 in snow

  19. 32Bristol, Maine

    Better for a vacation home than 100% of U.S. towns

    2,834 people · Lincoln County · median home $406,400 · income $100,750 · Jan low 15°F · 70 in snow

  20. 31Southern Shores, North Carolina

    Better for a vacation home than 100% of U.S. towns

    3,090 people · Dare County · median home $712,300 · income $131,429 · Jan low 36°F · 1 in snow

  21. 30Monmouth Beach, New Jersey

    Better for a vacation home than 100% of U.S. towns

    3,174 people · Monmouth County · median home $995,000 · income $150,188 · Jan low 25°F · 25 in snow

  22. 29Belgrade, Maine

    Better for a vacation home than 100% of U.S. towns

    3,250 people · Kennebec County · median home $312,200 · income $88,338 · Jan low 9°F · 87 in snow

  23. 28Shelter Island, New York

    Better for a vacation home than 100% of U.S. towns

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

  24. 27North Falmouth, Massachusetts

    Better for a vacation home than 100% of U.S. towns

    3,293 people · Barnstable County · median home $715,300 · income $121,509 · Jan low 22°F · 37 in snow

  25. 26Narragansett Pier, Rhode Island

    Better for a vacation home than 100% of U.S. towns

    3,308 people · Washington County · median home $851,300 · income $82,192 · Jan low 19°F · 35 in snow

  26. 25Ponce Inlet, Florida

    Better for a vacation home than 100% of U.S. towns

    3,364 people · Volusia County · median home $544,300 · income $102,200 · Jan low 52°F · 0 in snow

  27. 24Grantham, New Hampshire

    Better for a vacation home than 100% of U.S. towns

    3,404 people · Sullivan County · median home $343,100 · income $106,403 · Jan low 9°F · 70 in snow

  28. 23West Tisbury, Massachusetts

    Better for a vacation home than 100% of U.S. towns

    3,555 people · Dukes County · median home $1,302,100 · income $182,750 · Jan low 23°F · 25 in snow

  29. 22Wellfleet, Massachusetts

    Better for a vacation home than 100% of U.S. towns

    3,566 people · Barnstable County · median home $855,300 · income $117,938 · Jan low 26°F · 23 in snow

  30. 21Big Sky, Montana

    Better for a vacation home than 100% of U.S. towns

    3,591 people · Gallatin County · median home $1,137,900 · income $138,805 · Jan low 9°F · 48 in snow

  31. 20Little Compton, Rhode Island

    Better for a vacation home than 100% of U.S. towns

    3,616 people · Newport County · median home $783,400 · income $134,750 · Jan low 24°F · 38 in snow

  32. 19Westhampton, New York

    Better for a vacation home than 100% of U.S. towns

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

  33. 18Essex, Massachusetts

    Better for a vacation home than 100% of U.S. towns

    3,675 people · Essex County · median home $897,400 · income $157,147 · Jan low 18°F · 51 in snow

  34. 17South Beach, Florida

    Better for a vacation home than 100% of U.S. towns

    3,703 people · Indian River County · median home $900,700 · income $193,594 · Jan low 51°F · 0 in snow

  35. 16Camden, Maine

    Better for a vacation home than 100% of U.S. towns

    3,850 people · Knox County · median home $498,800 · income $78,788 · Jan low 12°F · 69 in snow

  36. 15Vineyards, Florida

    Better for a vacation home than 100% of U.S. towns

    3,883 people · Collier County · median home $651,800 · income $131,118 · Jan low 52°F · 0 in snow

  37. 14Beach Haven West, New Jersey

    Better for a vacation home than 100% of U.S. towns

    4,143 people · Ocean County · median home $641,700 · income $119,394 · Jan low 27°F · 10 in snow

  38. 13Indian River Shores, Florida

    Better for a vacation home than 100% of U.S. towns

    4,241 people · Indian River County · median home $1,132,000 · income $156,037 · Jan low 54°F · 0 in snow

  39. 12Highland Beach, Florida

    Better for a vacation home than 100% of U.S. towns

    4,295 people · Palm Beach County · median home $909,200 · income $145,485 · Jan low 56°F · 0 in snow

  40. 11Montauk, New York

    Better for a vacation home than 100% of U.S. towns

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

  41. 10Northwest Harbor, New York

    Better for a vacation home than 100% of U.S. towns

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

  42. 9Butler Beach, Florida

    Better for a vacation home than 100% of U.S. towns

    4,978 people · St. Johns County · median home $493,100 · income $76,689 · Jan low 48°F · 0 in snow

  43. 8Bar Harbor, Maine

    Better for a vacation home than 100% of U.S. towns

    5,089 people · Hancock County · median home $538,400 · income $77,180 · Jan low 15°F

  44. 7Camden, Maine

    Better for a vacation home than 100% of U.S. towns

    5,232 people · Knox County · median home $520,600 · income $82,344 · Jan low 12°F · 69 in snow

  45. 6Rye, New Hampshire

    Better for a vacation home than 100% of U.S. towns

    5,543 people · Rockingham County · median home $1,028,100 · income $140,655 · Jan low 16°F · 65 in snow

  46. 5Jamestown, Rhode Island

    Better for a vacation home than 100% of U.S. towns

    5,559 people · Newport County · median home $842,400 · income $140,625 · Jan low 24°F · 26 in snow

  47. 4Eastham, Massachusetts

    Better for a vacation home than 100% of U.S. towns

    5,752 people · Barnstable County · median home $732,200 · income $72,992 · Jan low 26°F · 24 in snow

  48. 3Woodstock, New York

    Better for a vacation home than 100% of U.S. towns

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

  49. 2Chatham, Massachusetts

    Better for a vacation home than 100% of U.S. towns

    6,594 people · Barnstable County · median home $942,800 · income $85,167 · Jan low 25°F · 25 in snow

  50. 1Pelican Bay, Florida

    Better for a vacation home than 100% of U.S. towns

    6,660 people · Collier County · median home $1,287,900 · income $163,520 · Jan low 56°F · 0 in snow

Price vs ranking

Median home value vs ranking, U.S. towns0255075100$37K$341K$645K$948K$1252KMedian home valuePercentile
Orange squares are the 50 towns on this list; green dots are other towns on The Town Files in the U.S..

More U.S. rankings

Same ranking, other places

Methodology. We ranked 7,696 towns of 2,500–10,000 people in the U.S. (2020 Census population; towns with 2,500+ people have pages so far). Lifestyle measures are The Town Files lifestyle rankings, built from federal demographic, school, crime and housing data (2025), shown as percentiles. Only towns better than 60% of their peers on this measure qualify, so lists can be shorter than 25. Sources: