Search Holiday Rentals in Annapolis

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Top Holiday Rentals in Annapolis

Sam A Baker State Park
Cabin | 5 bedrooms

Sam A Baker State Park

2.0 star property
9.0 out of 10, Wonderful, (4)
"Pet friendly, great staff. "
The price is 3.299.500 ₫
3.496.645 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Sam A Baker State Park
Johnson's Shut-ins State Park
Full-sized fridge, microwave, oven, stovetop

Johnson's Shut-ins State Park

3.0 star property
The price is 7.390.880 ₫
7.814.008 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Johnson's Shut-ins State Park
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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Top Annapolis Hotel Reviews

Shepherd Mountain Inn

Shepherd Mountain Inn

10/10 Excellent
"Everything was wonderful- the family that owns this is very kind, and it’s in a beautiful location!"
Nathan 1-night trip
Posted 7 days ago
Shepherd Mountain Inn

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?

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