101+ Rental Villas and Private Getaways in Winchester |
  1. USA
  2. Massachusetts
  3. Boston
  4. Winchester

Winchester Villa Rentals

About Winchester Vacation Rentals

There are more than 101 incredible getaway rentals that are available in Winchester. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Winchester.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Winchester, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Winchester. Places to stay near Winchester are 593.22 ft² on average, with prices averaging US $363 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Winchester. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Show more
Show less

Top Private Villas, Resorts, and Rentals in Winchester

Type Count
Holiday Apartments 44
Vacation Homes 43
Cottages 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Winchester

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Winchester with BedroomVillas.

Weather in Winchester, MA

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Winchester's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Winchester's Research Top Attractions For Your Vacation


Winter Pond
Winchester Hospital
Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center
Massachusetts Institute of Technology
Copley Place
Boston Children's Museum

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Winchester Hospital 136 Properties
Winter Pond 92 Properties

Frequently Asked Questions About Winchester?

What are the top hotels or resorts in Winchester?

We provide an array of great vacation destinations in Winchester. If you are looking to stay in or around the Winchester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winchester:

Which hotel or resort in Winchester is best for families?

Searching for a family-friendly getaway in Winchester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Winchester?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 101 in the Winchester area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Winchester. 


People Also Ask

There are 6 hotels in Winchester and 87 rentals

Recently Booked Hotels, Resorts, or Rentals in Winchester