Compare Annapolis Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Annapolis

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Kitchen

Washer

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.

This cottage offers a picnic area, a garden, and barbecue grills.

Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.

Hot Tub

Breakfast included

Secluded Cozy Cottage in Historic Downtown

$657 nightly

$749 total

Aug 10 - Aug 11

Total with taxes and fees

At this cottage, guests have access to a terrace, laundry facilities, and a garden. If you drive, put free offsite parking to good use. This smoke-free cottage also has barbecue grills.

Kitchen

Washer

1 Block to Usna Stadium: Modern Annapolis Home!

This cottage features free WiFi in public areas and barbecue grills. A stay here includes free parking.

Kitchen

Washer

Waterfront Annapolis Cottage: Fire Pit & Pier

This cottage features free WiFi in public areas and barbecue grills.

Kitchen

Dryer

Walk to Everything - Historic Art’s District

At this cottage, guests have access to features like laundry facilities.

Kitchen

Washer

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

This cottage features free WiFi in public areas and barbecue grills. You can take advantage of free parking if you drive.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Annapolis

View all properties

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.

Hotel Options in Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$98 nightly

$111 total

Aug 30 - Aug 31

Total with taxes and fees

8.8/10 Excellent! (1,084 reviews)

Historic Inns of Annapolis

58 State Circle Annapolis MD

$132 nightly

$150 total

Aug 19 - Aug 20

Total with taxes and fees

9/10 Wonderful! (1,932 reviews)

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

$110 nightly

$125 total

Sep 1 - Sep 2

Total with taxes and fees

Cottages

Book a cottage in Annapolis
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Annapolis. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Annapolis better.

Cottage apartments in Annapolis range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Annapolis
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Annapolis and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Annapolis cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Annapolis. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Annapolis Cottages essential information

Accommodation	13 Cottages
Lowest Price	$111
Highest Price	$749
Popular accommodation	Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly, The Yellow Cottage on Harness Creek, Your Annapolis Waterfront retreat for a weekend or any-day getaway! Great lodging for Plebe Parent's Weekend - and all your USNA activities., Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA games., Secluded Cozy Cottage in Historic Downtown, 1 Block to Usna Stadium: Modern Annapolis Home!, Waterfront Annapolis Cottage: Fire Pit & Pier, Walk to Everything - Historic Art’s District, Annapolis Vacation Home: 2 Mi to Quiet Waters Park