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Compare 26 Vacation Homes in Annapolis with updated reviews, rates, and availability.

The Sutton House 2 blocks from Main Street & Courthouse Square
The Sutton House 2 blocks from Main Street & Courthouse Square
10.0 out of 10, Exceptional, (22)
The price is SAR 503
SAR 653 total
includes taxes & fees
16 Apr - 17 Apr

Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
10.0 out of 10, Exceptional, (28)
The price is SAR 492
SAR 886 total
includes taxes & fees
16 Apr - 17 Apr

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
10.0 out of 10, Exceptional, (59)

Historic Victorian close to amazing hiking - pet friendly!
Historic Victorian close to amazing hiking - pet friendly!
8.8 out of 10, Excellent, (6)

Newly remodeled offers many amenities with perfect location!
Newly remodeled offers many amenities with perfect location!
10.0 out of 10, Exceptional, (26)

Charming 1860s Renovated Home
Charming 1860s Renovated Home
8.0 out of 10, Very Good, (16)
The price is SAR 507
SAR 1,010 total
includes taxes & fees
16 Apr - 17 Apr

Charming Country Bungalow - perfect for families
Charming Country Bungalow - perfect for families
10.0 out of 10, Exceptional, (13)

Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks
10.0 out of 10, Exceptional, (5)
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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Other property types in Annapolis

Make your reservation fast as inquiries are coming in daily.
Make your reservation fast as inquiries are coming in daily.
9.8 out of 10, Exceptional, (52)

New Cabin Just Minutes from Black River
New Cabin Just Minutes from Black River
7.4 out of 10, Good, (3)
The price is SAR 486
SAR 944 total
includes taxes & fees
16 Apr - 17 Apr

Rustic River Cabin Getaway
Rustic River Cabin Getaway
9.6 out of 10, Exceptional, (70)
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.
Recent reviews of Annapolis hotels
Recent reviews of Annapolis hotels

Shepherd Mountain Inn
5/5 Excellent
"The owner was very nice. We had made a reservation for a room type that was being renovated and he gave us two adjoining rings instead since it was not busy. Good breakfast and friendly service. He provided recommendations for things to do and see. I would definitely go there again if I'm in the area. "
A verified traveler stayed at Shepherd Mountain Inn
Posted 12 days ago