Hot Annapolis Cottage Rates

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Featured Cottages in Annapolis

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Annapolis
When you stay at this cottage in Annapolis, you'll be on the beach, within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina.
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

annapolis
With a stay at this cottage, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Annapolis Bowl.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Amazing views, short walks to great dining!

Amazing views, short walks to great dining!

Annapolis
With a stay at this cottage in Annapolis (West Annapolis), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium.
Amazing views, short walks to great dining!
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Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Annapolis
With a stay at this cottage in Annapolis (West Annapolis), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium.
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

Annapolis
With a stay at this cottage in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Pet-friendly Annapolis Home: Walk to Beach!

Pet-friendly Annapolis Home: Walk to Beach!

3 out of 5
Annapolis
With a stay at this cottage in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Pet-friendly Annapolis Home: Walk to Beach!
6 Mi to Dtwn: Family-friendly Home in Annapolis!

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3 out of 5
Annapolis
With a stay at this cottage in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Broad Creek Marsh.
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Annapolis
The price is AU$1,200 per night from 6 Apr to 7 Apr
AU$1,200
includes taxes & fees
6 Apr - 7 Apr
With a stay at this cottage in Annapolis (Historic District), you'll be within a 15-minute walk of U.S. Naval Academy and 14 Fleet Street.
Secluded Cozy Cottage in Historic Downtown
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Annapolis
With a stay at this cottage in Annapolis (Hillsmere), you'll be within a 15-minute drive of U.S. Naval Academy and Maryland Quiet Waters Park.
The Yellow Cottage on Harness Creek
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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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Annapolis will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Annapolis definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Annapolis, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Annapolis Cottages essential information

Accommodation
18 Cottages
Lowest Price
AU$153
Highest Price
AU$1,200
Popular accommodation
Waterfront dog-friendly home with beach just mins to Downtown Annapolis, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Amazing views, short walks to great dining!, Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking, , Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break , Pet-friendly Annapolis Home: Walk to Beach!, 6 Mi to Dtwn: Family-friendly Home in Annapolis!, Secluded Cozy Cottage in Historic Downtown, The Yellow Cottage on Harness Creek

Top trending hotels in Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$318 per night from 13 Apr to 14 Apr
AU$318
includes taxes & fees
13 Apr - 14 Apr
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 6 Apr to 7 Apr
AU$272
includes taxes & fees
6 Apr - 7 Apr
With a stay at The Westin Annapolis in Annapolis, you'll be in the historical district, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill ...
The Westin Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is AU$201 per night from 22 Apr to 23 Apr
AU$201
includes taxes & fees
22 Apr - 23 Apr
Located in Annapolis, Crowne Plaza Annapolis by IHG is a 4-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical ...
Crowne Plaza Annapolis by IHG
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Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 20 Apr to 21 Apr
AU$153
includes taxes & fees
20 Apr - 21 Apr
With a stay at Hilton Garden Inn Annapolis Downtown, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil ...
Hilton Garden Inn Annapolis Downtown
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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.

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^Subject to availability and chosen travel dates.