Hotels in Winchester-on-the-Severn

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Dec 19 - Dec 20
Tomorrow
Dec 20 - Dec 21
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Where to stay in Winchester-on-the-Severn?

Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
4.3 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1008)
The price is CNY605
CNY690 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hilton Garden Inn Annapolis Downtown
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.
See more propertiesforward arrow

When is the best time to visit Annapolis?

Our prices for hotels in Annapolis are cheapest in March
Price trends for hotels in Annapolis
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Annapolis
December
Moderate crowds
High 8°C / low 3°C. Partly sunny.
View properties in December
8°
weather_partly_sunny
December, Moderate crowds, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
5°
weather_partly_sunny
January, Low crowds, average high temperature 5 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
7°
weather_partly_sunny
February, Low crowds, average high temperature 7 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
0°
11°
weather_partly_sunny
March, Low crowds, average high temperature 11 degrees Celsius, average low temperature 4 degrees Celsius. Partly sunny.
4°
17°
weather_sun
April, Low crowds, average high temperature 17 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
9°
22°
weather_sun
May, High crowds, average high temperature 22 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
26°
weather_sun
June, High crowds, average high temperature 26 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
29°
weather_sun
July, High crowds, average high temperature 29 degrees Celsius, average low temperature 23 degrees Celsius. Sunny most days.
23°
28°
weather_sun
August, High crowds, average high temperature 28 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
22°
25°
weather_sun
September, Moderate crowds, average high temperature 25 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
19°
weather_sun
October, Moderate crowds, average high temperature 19 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
13°
13°
weather_sun
November, Moderate crowds, average high temperature 13 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
6°
Monthly weather averages (˚C)

Check out reviews of Winchester-on-the-Severn hotels guests love

Days Inn & Suites by Wyndham Laurel Near Fort Meade

Days Inn & Suites by Wyndham Laurel Near Fort Meade

10/10 Excellent
"Rating: ★★☆☆☆ (2 out of 5 stars) My stay began poorly due to a booking miscommunication between the hotel and its partner site, which left me waiting nearly 40 minutes before check‑in. The first room was unacceptable: the bed was defective, the temperature was uncomfortably cold, the bathroom lacked soap, and the parking lot was icy, dark, and unsafe. Basic amenities such as a microwave and refrigerator were missing. Fortunately, Robin at the front desk provided outstanding service. She upgraded me to a suite, ensured I had proper amenities, and even supplied dining essentials. Her professionalism and kindness salvaged the experience. Summary: While the property requires significant improvements in communication, maintenance, and guest readiness, Robin’s exceptional service prevented this from being a one‑star stay. "
Babette 1-night trip
Posted 1 day ago
Days Inn & Suites by Wyndham Laurel Near Fort Meade

Frequently asked questions

Is Winchester-on-the-Severn expensive to stay in?
You can find great hotels from CNY599 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?
Discover great deals on hotels in Winchester-on-the-Severn with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Winchester-on-the-Severn hotels.
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.
Find out more about Winchester-on-the-Severn

Keep exploring