Winchester vacation rentals

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Best Winchester vacation rentals

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$0 - $43$43 - $86$86 - $129$129 - $171$171+ per night

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Most recommended vacation rentals in Winchester

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Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93 - Winchester - Dining room
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Winchester, MA
Free Wi-Fi
$171+
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Good to know

Low season

High season

Average price (weeknight)

February
May
$121
Cheapest month to stay with an average 10% drop in price.
Most expensive month to stay with an average 27% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Winchester vacation rental deals

  • If you’re looking for a cheap vacation rental in Winchester, you should consider visiting during the low season. The cheapest vacation homes in Winchester can be found in February and April.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winchester for 24 days.

FAQs when booking a vacation home in Winchester

  • What types of vacation rentals are available in Winchester?

    in Winchester you’ll find that most vacation rentals are apartments.

  • How can I find vacation rentals near me in Winchester?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Winchester?

Our map will help you find the perfect place to stay in Winchester by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Winchester

Winchester vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Winchester. Find cheap vacation homes to rent in Winchester. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Winchester that suits you best.

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