Compare Annapolis Cottage Rentals

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Featured Annapolis Cottages

Secluded Cozy Cottage in Historic Downtown

$506 nightly

$577 total

Jan 5 - Jan 6, 2026

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.

Kitchen

Washer

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

Kitchen

Washer

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

Hot Tub

Breakfast included

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

Hot Tub

Kitchen

Beachfront Home Minutes to Downtown Annapolis Dogs OK

At this cottage, guests have access to a gym, laundry facilities, and a garden. This beach cottage also has barbecue grills.

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

Parking included

Waterfront Annapolis Home: Fire Pit & Fishing Pier

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

Kitchen

Pet friendly

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

Washer

Dryer

Your Annapolis Waterfront retreat - ready for a November or December Annapolis getaway!

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

Kitchen

Free WiFi

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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.

Annapolis Beach Accommodation

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

$203 nightly

$232 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

8.8/10 Excellent! (886 reviews)

Hotel Options in Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$75 nightly

$85 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

8.6/10 Excellent! (1,014 reviews)

Historic Inns of Annapolis

58 State Circle Annapolis MD

$169 nightly

$193 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

8.8/10 Excellent! (1,907 reviews)

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

$106 nightly

$121 total

Jan 25 - Jan 26, 2026

Total with taxes and fees

8.6/10 Excellent! (1,004 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	15 Cottages
Lowest Price	$85
Highest Price	$577
Popular accommodation	Secluded Cozy Cottage in Historic Downtown, The Yellow Cottage on Harness Creek, Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Beachfront Home Minutes to Downtown Annapolis Dogs OK, Annapolis Vacation Home: 2 Mi to Quiet Waters Park, Waterfront Annapolis Home: Fire Pit & Fishing Pier, The Red Door Cottage in Eastport - Pet-Friendly!, Your Annapolis Waterfront retreat - ready for a November or December Annapolis getaway!