Hotels in Winchester-on-the-Severn

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Our prices for Annapolis are cheapest in January

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Weather forecast for Annapolis
September
trending_flatModerate crowds
High 77°F / low 65°F. Sunny most days.
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September, Moderate crowds, average high temperature 77 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
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66°
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October, Moderate crowds, average high temperature 66 degrees Fahrenheit, average low temperature 55 degrees Fahrenheit. Sunny most days.
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55°
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November, Moderate crowds, average high temperature 55 degrees Fahrenheit, average low temperature 43 degrees Fahrenheit. Sunny most days.
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46°
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December, Moderate crowds, average high temperature 46 degrees Fahrenheit, average low temperature 37 degrees Fahrenheit. Partly sunny.
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January, Low crowds, average high temperature 41 degrees Fahrenheit, average low temperature 31 degrees Fahrenheit. Partly sunny.
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February, Low crowds, average high temperature 44 degrees Fahrenheit, average low temperature 32 degrees Fahrenheit. Partly sunny.
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March, Low crowds, average high temperature 51 degrees Fahrenheit, average low temperature 38 degrees Fahrenheit. Partly sunny.
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April, Low crowds, average high temperature 62 degrees Fahrenheit, average low temperature 48 degrees Fahrenheit. Sunny most days.
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71°
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May, High crowds, average high temperature 71 degrees Fahrenheit, average low temperature 58 degrees Fahrenheit. Sunny most days.
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June, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 67 degrees Fahrenheit. Sunny most days.
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July, High crowds, average high temperature 85 degrees Fahrenheit, average low temperature 73 degrees Fahrenheit. Sunny most days.
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August, High crowds, average high temperature 83 degrees Fahrenheit, average low temperature 71 degrees Fahrenheit. Sunny most days.
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Monthly weather averages (˚F)

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Frequently asked questions

Is Winchester-on-the-Severn expensive to stay in?
You can find great hotels from $87 in Winchester-on-the-Severn to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Winchester-on-the-Severn hotels?
Unlocking discounted rates at hotels in Winchester-on-the-Severn couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
Can I receive a refund if I cancel my Winchester-on-the-Severn hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Winchester-on-the-Severn hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
Is it worth staying in Winchester-on-the-Severn?
Basing yourself in Winchester-on-the-Severn makes it easy to explore Annapolis, including the neighborhoods of Historic District and Eastport.
Are all taxes and fees included in the Winchester-on-the-Severn hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.

Find out more about Winchester-on-the-Severn

Find out more about Winchester-on-the-Severn

Winchester-on-the-Severn: Where Scenic Shores Meet Historic Bridges

Nestled along the serene shores of the Severn River, Winchester-on-the-Severn is a hidden gem of Annapolis, Maryland. This picturesque haven offers a unique blend of natural beauty and charming waterfront living. Stroll along scenic paths, enjoy breathtaking views, and relax on tranquil beaches. The area is perfect for romantic getaways or peaceful retreats, with ample opportunities for kayaking, fishing, and birdwatching. Nearby, the historic charm of downtown Annapolis beckons with its vibrant arts scene and delightful restaurants. Experience the allure of this enchanting destination, where nature and culture beautifully intertwine.

Discover great hotels in Winchester-on-the-Severn

Winchester-on-the-Severn offers a variety of accommodations, from cozy house rentals to charming vacation homes, perfect for enjoying the scenic waterfront. Whether you're seeking a quaint B&B or a spacious rental for the family, you'll find options that cater to a relaxed and enjoyable stay. These are some of the hotels preferred by our travelers in Winchester-on-the-Severn:

  1. Village InnOpens in a new window: Village Inn is a cozy 2.0-star motel designed for travelers seeking a family-friendly getaway. With a welcoming atmosphere, this property features amenities like complimentary cribs, making it perfect for those traveling with little ones. The pet-friendly policy adds an extra layer of comfort, allowing guests to bring their furry companions along. Positive sentiments highlight the warm environment and the convenience of family-oriented services, ensuring a pleasant stay for all.
  2. Rodeway InnOpens in a new window: Rodeway Inn offers a delightful 2.0-star motel experience, ideal for leisure travelers looking for value and comfort. Guests can indulge in complimentary breakfast options while enjoying a casual ambiance at the bar and lounge. With entertainment amenities such as cable television, this hotel creates a relaxed atmosphere perfect for unwinding after a day of exploration. Positive feedback emphasizes the enjoyable breakfast offerings and the overall comfortable stay, making it a favorite among travelers.
  3. Quality InnOpens in a new window: Quality Inn is an elevated 2.5-star hotel that caters to discerning travelers seeking a balanced blend of comfort and convenience. This property stands out with its business center, making it suitable for those who may need to attend to work matters during their stay. The family-friendly amenities, including complimentary cribs, ensure that every guest feels at home. Positive reviews highlight the seamless experience and thoughtful services that enhance the overall stay, making it a preferred choice for both leisure and business travelers.

Top locations to stay in Winchester-on-the-Severn

Staying in Winchester-on-the-Severn, Annapolis, Maryland, near the U.S. Naval Academy, Chesapeake Bay Bridge, and Sandy Point State Park offers diverse attractions. The U.S. Naval Academy features rich history and maritime culture, the Chesapeake Bay Bridge boasts stunning views and easy access to the bay, while Sandy Point State Park is perfect for outdoor activities. For first-time visitors, staying near the U.S. Naval Academy is best for its unique educational experience and vibrant atmosphere.

  1. Near U.S. Naval AcademyOpens in a new window: Staying near the U.S. Naval Academy puts you right at the heart of Annapolis, where you can soak in the rich maritime history and stunning architecture. Explore cultural attractions like the Annapolis Maritime Museum and enjoy scenic views around the harbor. You'll also find great shopping options at Annapolis Mall Shopping Center and Westfield Annapolis Mall, perfect for picking up souvenirs or treating yourself.
  2. Near Chesapeake Bay BridgeOpens in a new window: This iconic bridge is not just a stunning landmark; staying nearby gives you easy access to breathtaking views and outdoor activities. Enjoy a day at Sandy Point Beach or venture into the natural beauty of Sandy Point State ParkOpens in a new window, ideal for picnics and nature walks. You’ll also appreciate the variety of cultural venues and local shops in the area, making it a vibrant spot to explore.
  3. Near Sandy Point State Park: With its beautiful beaches and hiking trails, staying near Sandy Point State Park offers a perfect blend of relaxation and outdoor fun. The park is a great place for families to enjoy a day out, while the surrounding area has plenty of shopping options like Annapolis Harbor Center Shopping Center. You can also catch a cultural event at nearby venues, adding a delightful experience to your stay.

Things to do near Winchester-on-the-Severn

Winchester-on-the-Severn boasts stunning beaches and picturesque waterways, ideal for boating and diving adventures. With scenic parks for leisurely strolls and vibrant shopping centers offering local treasures, it's a delightful spot for relaxation and exploration. Enjoy outdoor recreation while soaking in the serene coastal charm.

  • Rock Hall HarborOpens in a new window – Spend a relaxing day at Rock Hall Harbor, where you can enjoy the picturesque views of the water and watch boats come and go. It’s a great spot for a peaceful stroll along the shoreline or for picnicking with family and friends while soaking in the natural beauty of the area.
  • Chesapeake Bay BridgeOpens in a new window – Drive across the iconic Chesapeake Bay Bridge, a modern engineering marvel that spans the bay. Stop at designated viewing areas to take in the stunning vistas that stretch across the water, offering perfect photo opportunities and a chance to appreciate the bridge's impressive architecture.
  • Sandy Point State ParkOpens in a new window – Explore Sandy Point State Park, where sandy beaches meet lush greenery. Pack a lunch and enjoy a day of swimming, sunbathing, or hiking along the scenic trails. The park is perfect for families looking to partake in outdoor activities like birdwatching or simply enjoying a day in nature.
  • Six Flags AmericaOpens in a new window – Get your adrenaline pumping at Six Flags America, an amusement park filled with thrilling rides and exciting attractions. From roller coasters to live entertainment, there’s something for everyone. Enjoy a day of laughter and adventure, making unforgettable memories with family or friends.

5 tips for savvy savings when booking a hotel in Winchester-on-the-Severn

  1. Book for the cheapest times: The most affordable time to visit Winchester-on-the-Severn is during January, February, and December, when hotel prices tend to be lower. For an enriching experience, it's recommended to stay for at least 2 to 3 days to fully explore the area's notable landmarks, cultural sites, and historical attractions. This budget-friendly trip could include visits to modern bridges, monuments, urban parks, and shopping centers, as well as opportunities to engage with local education and events at conference venues. Enjoying everything Winchester-on-the-Severn has to offer can provide great value for money while you're on a budget.
  2. Look for last-minute deals on Hotels.com: To explore last-minute deals to Winchester-on-the-Severn, you may want to check the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you could find discounted hotel rates as your travel date approaches. To enhance your chances of savings, consider enabling email alerts or push notifications for flash sales and special promotions. Hotels.com will keep you informed about price changes and availability for your preferred hotels. Additionally, the Smart ShoppingOpens in a new window feature allows you to compare hotel prices and amenities, helping you make informed decisions and possibly secure a great last-minute getaway.
  3. Be flexible with dates: Prices can fluctuate due to factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates could help you save on your stay at a hotel in Winchester-on-the-Severn. For those seeking unique accommodations, boutique hotels can provide a more personalized experience and sometimes better value. When you book through Hotels.com, we'll inform you if the price for your chosen dates is above or below the average. If the price is on the higher side, we’ll recommend more affordable dates, increasing the chances that you could save on your trip.
  4. Consider your location: Choosing accommodations near major attractions or city centers can be convenient, but they usually tend to be more expensive. For more budget-friendly options, look for hotels in less central areas or neighborhoods that strike a balance between cost and accessibility to the sites you plan to visit. You might also consider independent hotels located a bit further out, as they can offer a more authentic experience while still being budget-conscious.
  5. Become a Member: Join our membership program for free and start planning your next stay in Winchester-on-the-Severn! Enjoy exclusive member prices and save on over 100,000 hotels worldwide. As a valued member, you’ll have the opportunity to advance through our tiers, unlocking fantastic perks such as complimentary room upgrades when available and discounts on food and beverages at select VIP Access properties. Don’t miss out on these incredible benefits—sign up today and make your next trip even more enjoyable!

What's Winchester-on-the-Severn Like?

If you're in search of the perfect area to explore, look no further than Winchester-on-the-Severn. Places to visit like Navy-Marine Corps Memorial Stadium and Maryland State House are not far away. William Paca House and U.S. Naval Academy Golf Club are two places to visit nearby.

How to Get to Winchester-on-the-Severn

Flying to:

  • Baltimore Washington Intl. Airport (BWI), 14.3 mi (23 km) from Winchester-on-the-Severn
  • Fort Meade, MD (FME-Tipton), 14.5 mi (23.3 km) from Winchester-on-the-Severn
  • Baltimore, MD (MTN-Martin State), 22.1 mi (35.6 km) from Winchester-on-the-Severn

Things to See and Do in and around Winchester-on-the-Severn

Things to See near Winchester-on-the-Severn:

  • Navy-Marine Corps Memorial Stadium (2.1 mi/3.4 km away)
  • U.S. Naval Academy (2.4 mi/3.8 km away)
  • Maryland State House (2.7 mi/4.3 km away)
  • William Paca House (2.7 mi/4.3 km away)
  • Ego Alley (2.9 mi/4.7 km away)

Things to Do near Winchester-on-the-Severn:

  • U.S. Naval Academy Golf Club (2.7 mi/4.3 km away)
  • Westfield Annapolis Mall (2.7 mi/4.4 km away)
  • Annapolis Mall Shopping Center (2.7 mi/4.4 km away)
  • Annapolis City Dock (2.8 mi/4.5 km away)
  • Maryland Hall for Creative Arts (2.9 mi/4.7 km away)

When Is the Best Time to Visit Annapolis?

  • Hottest months: July, August, June, September (average 75°F)
  • Coldest months: January, February, December, March (average 40°F)
  • Rainiest months: July, September, August, October (average 5 inches of rainfall)

Winchester-on-the-Severn Travel Information

Best Time to Visit
March, July and August
Average Stay
2 days
Closest Neighborhoods
Historic District, Oyster Harbor
Top Attractions
U.S. Naval Academy, Maryland State House, William Paca House

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