Compare Annapolis Cottage Rentals

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Featured Cottages in Annapolis

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

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

Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

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

Your Annapolis Waterfront retreat for a weekend or any-day getaway!

$408 nightly

$459 total

Nov 5 - Nov 6

Total with taxes and fees

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

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

Secluded Cozy Cottage in Historic Downtown

$714 nightly

$814 total

Nov 8 - Nov 9

Total with taxes and fees

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

Walk to Everything - Historic Art’s District

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

The Red Door Cottage in Eastport - Pet-Friendly!

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

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.

Waterfront Annapolis Cottage: Fire Pit & Pier

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

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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

Graduate by Hilton Annapolis

126 West St Annapolis MD

$147 nightly

$167 total

Oct 26 - Oct 27

Total with taxes and fees

9.4/10 Exceptional! (1,000 reviews)

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$111 nightly

$126 total

Oct 20 - Oct 21

Total with taxes and fees

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

$106 nightly

$121 total

Nov 15 - Nov 16

Total with taxes and fees

8.8/10 Excellent! (1,002 reviews)

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	14 Cottages
Lowest Price	$121
Highest Price	$814
Popular accommodation	Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly, Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football., Your Annapolis Waterfront retreat for a weekend or any-day getaway!, The Yellow Cottage on Harness Creek, Secluded Cozy Cottage in Historic Downtown, Walk to Everything - Historic Art’s District, The Red Door Cottage in Eastport - Pet-Friendly!, 1 Block to Usna Stadium: Modern Annapolis Home!, Waterfront Annapolis Cottage: Fire Pit & Pier