613+ Rental Villas and Private Getaways in Winchester-on-the-Severn |
  1. USA
  2. Maryland
  3. Annapolis
  4. Winchester-on-the-Severn

Winchester-on-the-Severn Villa Rentals

About Winchester-on-the-Severn Vacation Rentals

There are more than 613 incredible getaway rentals that are available in Winchester-on-the-Severn. 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-on-the-Severn.

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-on-the-Severn, 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-on-the-Severn. Places to stay near Winchester-on-the-Severn are 944.92 ft² on average, with prices averaging $604 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Winchester-on-the-Severn. 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-on-the-Severn

Type Count
Vacation Homes 476
Holiday Apartments 70
Cottages 12
B&B 3
Villas 3
Unique Vacation Rentals 2

Use these Quick Filters to Find a Vacation Rental in Winchester-on-the-Severn

★ 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-on-the-Severn with BedroomVillas.

Weather in Winchester-on-the-Severn, MD

View the weather forecast for Winchester-on-the-Severn before booking your Winchester-on-the-Severn 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

Frequently Asked Questions About Winchester-on-the-Severn?

What are the top hotels or resorts in Winchester-on-the-Severn?

We provide an array of great vacation destinations in Winchester-on-the-Severn. If you are looking to stay in or around the Winchester-on-the-Severn 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-on-the-Severn:

How many vacation rentals have private pools in Winchester-on-the-Severn?

We have 5 luxury villas and vacation rentals featuriung a private pool in and near Winchester-on-the-Severn. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Winchester-on-the-Severn is best for families?

Searching for a family-friendly getaway in Winchester-on-the-Severn? 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-on-the-Severn?

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 613 in the Winchester-on-the-Severn 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-on-the-Severn. 


People Also Ask

There are 35 hotels in Winchester-on-the-Severn 1 resorts, and 549 rentals

Recently Booked Hotels, Resorts, or Rentals in Winchester-on-the-Severn