Search Holiday Rentals in Annapolis

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Top Holiday Rentals in Annapolis

Other types of properties in Annapolis you may be interested in

Madison Inn Lodge
2.5 star property
7.4 out of 10, Good, (228)
"Nice place will be a repeat customer."
The price is 2.214.330 ₫
2.418.479 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Madison Inn Lodge
Shepherd Mountain Inn
2.5 star property
9.2 out of 10, Wonderful, (220)
"very clean, staff was very nice, restaurant was very good, complimentary breakfast was adequate but not great. would recommend and we hope to stay here again in the future. We very much enjoyed our one night stay and wished we could have stayed longer"
The price is 2.634.593 ₫
2.877.688 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Shepherd Mountain Inn
Black River Motel and Restaurant
2.0 star property
10.0 out of 10, Exceptional, (4)
"Customer Service was great. This location was very clean with a nice cabin feel to it. A restaurant conveniently located below. Nice patio to hang out and play games. Met some awesome people at the motel. Being Father's Day weekend was awesome and the weather was hot. Perfect for swimming at Johnston shut-ins state park about 10min drive. Beautiful area to enjoy time with friends and family. Thank you for the hospitality. "
The price is 3.103.092 ₫
3.280.744 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Black River Motel and Restaurant
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.

Frequently asked questions

Can I find a holiday rental in Annapolis?

Yes, there are holiday rentals close to the most popular sights in Annapolis, or you can select a more secluded option if you're looking for a relaxing stay. Annapolis is known for its riverfront and parks. Make sure you have time to check out the restaurants while you're in the area.

How many holiday rentals are there in Annapolis?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Annapolis stay.

What can I see and do in Annapolis?

Taum Sauk Mountain State Park and Mark Twain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, K Bridge Recreation Area and Walnut Hollow Lake are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.