Find Romantic Hotels in Winchester-on-the-Severn, Annapolis

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester-on-the-Severn Romantic Hotels

Tonight
Aug 6 - Aug 7
Tomorrow
Aug 7 - Aug 8
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Winchester-on-the-Severn Romantic Hotels

Top Winchester-on-the-Severn Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Charming spot close to everything with excellent amenities and service. "
Jonathan 1-night trip
Posted 2 days ago
Graduate by Hilton Annapolis

Frequently asked questions

Searching for romantic hotels in Winchester-on-the-Severn?
If you and your partner need some romantic time away, we've got just the ticket. If you want to see some sights and attractions in the greater Winchester-on-the-Severn area, you might head to Arundel Mills Mall, Navy-Marine Corps Memorial Stadium, or William Paca House. If you'd like to stay close to a particular destination, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time to visit Winchester-on-the-Severn?
The hottest months are usually July and August with an average temperature of 75°F,
  • Coldest months: January, February, December, and March
  • Driest months: November, January, February, and March
  • Rainiest months: July, September, August, and October
What is there to do in Winchester-on-the-Severn?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Winchester-on-the-Severn has to offer. There's plenty to see in the greater Annapolis area, so you might plan to visit Arundel Mills Mall, Navy-Marine Corps Memorial Stadium, or William Paca House.