A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

Search Annapolis Guest Houses

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

Our top choices for Annapolis guest houses

An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

1. The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (168 reviews)
"The best vacation ever. Location is everything. Just a slice of heaven on earth. We will never top this stay. Tried to book a reservation before we left. Will return as often as possible."
United States
William
The price is AU$293
includes taxes & fees
13 Oct - 14 Oct
The Tilghman Island Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annapolis Hotel Reviews

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"It was ok - being renovated - parking ok - leaving and entering parking lot from 1 direction only - u turns needed to get in - all amenities close by"
William 3-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Annapolis by IHG

Find out more about Annapolis

Annapolis Guest Houses information

Number of reviews
168
Accommodation
2 Guest Houses
Lowest Price
AU$293
Highest Price
AU$293