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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Annapolis

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (164)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is NZ$1,281
includes taxes & fees
15 Aug - 16 Aug
Secluded Cozy Cottage in Historic Downtown
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
On the beach, sun-loungers, beach towels

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

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

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
2 Mi to Sandy Point State Park: Home w/ Deck!
Interior

2 Mi to Sandy Point State Park: Home w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean and nice. The beds choices were comfortable and keyless checkin was convenient. "
2 Mi to Sandy Point State Park: Home w/ Deck!
Perfect location for USNA Commissioning Week
Interior

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (84)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

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

9.8 out of 10, Exceptional, (29)
"Peaceful, quiet venue with hiking trails and a beautiful location! My family and I enjoyed the lovely home and downtown Annapolis where we savored delicious seafood and quality family-time. The hosts were responsive and the home was charming! Thank you for the terrific experience!"
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Annapolis Home Near Beach & Quiet Waters Park!
Interior

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Walk to Everything - Historic Art’s District
Exterior

Walk to Everything - Historic Art’s District

2.0 star property
Walk to Everything - Historic Art’s District
New Home w Luxe King Suite, Porch Vibes & Parking
Fridge, microwave, oven, stovetop

New Home w Luxe King Suite, Porch Vibes & Parking

New Home w Luxe King Suite, Porch Vibes & Parking
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Outdoor spa tub

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Interior

Walk to Lake & Boat Ramp: Central Gem in Annapolis

3.0 star property
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
Beach

Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.

Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great area and it was a perfect hotel for our trip. "
Lauren 3-night trip
Posted 4 hours ago
Graduate by Hilton Annapolis

Frequently asked questions

How much do cottages in Annapolis cost?
Cottages in Annapolis range between NZ$1,281 and NZ$1,281 per night. These properties offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Annapolis?
You can choose from 16 cottages in Annapolis. No matter if you're holidaying with the family or planning a weekend retreat with your buddies, Expedia can help you find the right place to reacquaint yourself with nature.
What is there to do in Annapolis near my cottage?
Annapolis has enough sights and activities to keep you busy for weeks (or months!), beginning with William Paca House. Maryland State House, Sandy Point State Park and U.S. Naval Academy Golf Club are other impressive attractions. If you're sticking around a while, Navy-Marine Corps Memorial Stadium and U.S. Naval Academy will put the finishing touches on your itinerary.