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Cottages in Annapolis

Beachfront Home Minutes to Downtown Annapolis Dogs OK
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

9.8 out of 10, Exceptional, (36)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (14)
"We had a very lovely stay . This is an excellent location . "
$657 nightly
The price is $749
Sep 28 - Sep 29
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (167)
"A lovely property in the perfect location! We will definitely rent again!"
The Yellow Cottage on Harness Creek
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
Exterior

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

10.0 out of 10, Exceptional, (96)
"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, Thanksgiving!
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!
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
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
House (4 Bedrooms) | Interior

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Annapolis Home Near Beach & Quiet Waters Park!
Terrace/patio

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games - <br>Navy v. South Florida 11/15/25 weekend still available!<br>Or the USNA Gospel Choir Concert weekend of 10/17/25
Exterior

Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games - <br>Navy v. South Florida 11/15/25 weekend still available!<br>Or the USNA Gospel Choir Concert weekend of 10/17/25

10.0 out of 10, Exceptional, (86)
"Nice small property. Great for get aways and amazing service."
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games - <br>Navy v. South Florida 11/15/25 weekend still available!<br>Or the USNA Gospel Choir Concert weekend of 10/17/25
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, (30)
"We loved staying at the cottage. The atmosphere was incredibly peaceful and relaxing and the setting beautiful. Isaac was very helpful and thoughtful in responding to our questions and requests. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
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
Exterior

New Home w Luxe King Suite, Porch Vibes & Parking

New Home w Luxe King Suite, Porch Vibes & Parking
Walk to Lake & Boat Ramp: Central Gem in Annapolis
House (4 Bedrooms) | 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.
Exterior

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

Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
2 Mi to Usna: Modern Annapolis Home w/ Fire Pit
House (2 Bedrooms) | Interior

2 Mi to Usna: Modern Annapolis Home w/ Fire Pit

3.0 star property
2 Mi to Usna: Modern Annapolis Home w/ Fire Pit
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

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"Very clean and updated. Wonderful staff too"
Walter 1-night trip
Posted 21 hours ago
Candlewood Suites Annapolis by IHG

Find out more about Annapolis

Find out more about Annapolis

Annapolis Cottages information

Number of reviews
380
Accommodation
15 Cottages
Lowest Price
$749
Highest Price
$749

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