0+ Bedrooms for 1+ Guests
Price  $10 - $1000+

Winchester Vacation Rentals and Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Winchester vacation homes and short term rentals from 8 rental sites including Booking, HomeAway, HomeStay and more, ranging from $30 to $700 a night. 
Showing 89 personalized results
    $150 / night
    Gorgeous 1 Bed 1 Bath
    Gorgeous 1 Bed 1 Bath
    1 bed / 1 bath
    Burlington, MA
    $150 / night
    Gorgeous 1 Bed 1 Bath
    Gorgeous 1 Bed 1 Bath
    1 bed / 1 bath
    Burlington, MA
    $80 / night
    Room with private entrance
    Room with private entrance
    1 bed / 1 bath
    Arlington, MA
    $265 / night
    Luxurious Comfort Home Close to T and Boston
    Luxurious Comfort Home Close to T and Boston
    2 bed / 1 bath
    Somerville, MA
    $320 / night
    4 BEDROOM LUXURIOUS, SPACIOUS  HOME IN BOSTON
    4 BEDROOM LUXURIOUS, SPACIOUS HOME IN BOSTON
    4 bed / 3 bath
    Winchester, MA
    $135 / night
    New 3 Bedroom- Soo close to Boston
    New 3 Bedroom- Soo close to Boston
    Studio
    Malden, MA
    $285 / night
    Luxurious Comfort  Home Close to T and Boston
    Luxurious Comfort Home Close to T and Boston
    2 bed / 1 bath
    Somerville, MA
    $285 / night
    Luxurious Comfort  Home Close to T and Boston
    Luxurious Comfort Home Close to T and Boston
    2 bed / 1 bath
    Somerville, MA
    $285 / night
    Brand New comfort Home Close to T and Boston
    Brand New comfort Home Close to T and Boston
    2 bed / 1 bath
    Somerville, MA
    $85 / night
    Close to colleges! Comfortable Room;
    Close to colleges! Comfortable Room;
    1 bed / 2 bath
    Lexington, MA

    Information about Winchester

    Vacation Rentals In Winchester

    Find the best Winchester vacation rentals with Tripping.com. Choose from 94 of rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $30 a night to $700 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 57 of homes in Winchester offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 17 rentals with pool or jacuzzi, or relax with the family in one of the 55 homes with cable TV.

    Search properties from 8 rental sites in Winchester where the top providers in that area are Booking, HomeAway, and TripAdvisor. There are 33 Booking rentals, 18 HomeAway short term rentals and 10 TripAdvisor vacation rentals.

    For all those dog lovers and cat lovers, Winchester offers 7 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.