Skip to main content

Cottages in Annapolis

Find the cottages that appeal to you the most

Select occupancy

The best cottages in Annapolis

Check out our selection of great cottages in Annapolis

Filter by:

Review score

Fisher House - Downtown Annapolis!

Annapolis

Fisher House - Downtown Annapolis! offers accommodations in Annapolis, 30 miles from Sports Legends Museum at Camden Yards and 30 miles from Baltimore Convention Center.

K
Karen
From
United States
The location is an easy and quick walk to The Naval Academy. The rooms are clean and well organized with plenty of bedding, pillows and towels. Everything is updated! There are even TVs in every room. We felt very much at home while attending our son’s Induction Day at The Naval Academy! We will definitely stay again for future visits.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 8 reviews
Price from
$740.93
1 night, 2 adults

Stylish + fresh bungalow 2 blocks from N-MC Stadium

Annapolis

Just a 11-minute walk from Navy-Marine Corps Memorial Stadium and 1.2 miles from Whitehall Gallery, Stylish + fresh bungalow 2 blocks from N-MC Stadium features accommodations in Annapolis with a...

C
Catherine
From
United States
Property was beautiful, everything was clean and well kept! Great location, only a 5 minute drive from downtown Annapolis. Very spacious for 6 people to sleep.
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 11 reviews
Price from
$440.40
1 night, 2 adults

The Ultimate cozy escape

Glen Burnie (Near Annapolis)

The Ultimate cozy escape is located in Glen Burnie, just 11 miles from Carroll Park and 12 miles from Sports Legends Museum at Camden Yards.

M
Maria
From
United States
Very nice, clean, convenient and perfect house. I will try to be back.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 13 reviews
Price from
$424.25
1 night, 2 adults

Welcome to our newly built house

Glen Burnie (Near Annapolis)

Welcome to our newly built house is located in Glen Burnie, just 12 miles from Pier Six Concert Pavilion and 12 miles from Harbor East Marina.

S
Stefani
From
United States
The place was very nice. It was clean and in great shape.
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 23 reviews
Price from
$385
1 night, 2 adults

Walk to the stadium, downtown, West St - close to everything

Annapolis

Walk to the stadium, downtown, West St - close to everything is located in Annapolis, just 2 miles from Annapolis Harbor and 29 miles from Sports Legends Museum at Camden Yards.

B
Brittany
From
United States
The property owner was very attentive, thoughtful, and very accessible. They truly thought about every possible need that we could use or needed. Had drinks ready in the fridge, snacks. It was like we were at home. Cozy and spacious, everyone had their own space, but amazing common area. Very close to everything. I’m absolutely in love with this property.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews

Historic Row Home 1 Block from Gate 1 at USNA

Annapolis

1.1 miles from Annapolis Harbor in Annapolis, Historic Row Home 1 Block from Gate 1 at USNA offers accommodations with access to a hot tub.

V
Venus
From
United States
The location was excellent. The house was very modern, clean, and had all of the amenities that you would want or need.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews

Weems Creek Cottage, Annapolis Waterfront

Annapolis

Weems Creek Cottage, Annapolis Waterfront offers accommodations in Annapolis, 29 miles from Sports Legends Museum at Camden Yards and 29 miles from Baltimore Convention Center.

F
Frances
From
United States
Absolutely gorgeous view! Location is close enough to walk downtown but far enough to be a quiet neighborhood. We even saw a fox on way out to explore one day!! The photo is the view from the window above the bed.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 12 reviews

Walk to Everything Historic Arts District

Annapolis

1.9 miles from Annapolis Harbor in Annapolis, Walk to Everything Historic Arts District provides accommodations with access to spa facilities, wellness packages, and beauty services.

A
Ann
From
United States
This charming , 2nd floor apartment was perfect for our girls weekend! The beds were comfortable, the kitchen well stocked and the place had a homey, seaside feel. Restaurants are around the corner and the harbor area is about a 15 minute walk . Off street parking for 2-3 cars was convenient.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 12 reviews

Vintage Charm: Annapolis Retreat

Annapolis

Offering a garden, Vintage Charm: Annapolis Retreat offers accommodations in Annapolis. The vacation home, set in a building dating from 1909, features free Wifi and free private parking.

T
Tara
From
United States
An extremely charming home in an excellent location. We parked the car and walked all over downtown Annapolis. The rooms were comfortable and the space was generous. Comparable price to the nicer hotels in town. Considering the privacy, the value was excellent.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 11 reviews

Neptune By The Water

Annapolis

Neptune By The Water offers accommodations in Annapolis, 10 miles from Annapolis Harbor and 26 miles from Sports Legends Museum at Camden Yards.

D
Diana
From
United States
We were 4 adults traveling for a funeral. It accommodated us very well, with two sitting spaces and an outdoor deck. One member of our group did not do steps well and was able to be accommodated by a door out of the basement. The basement was accommodated with a bedroom, full bathroom with walk in shower, a sitting area and the game space.
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 8 reviews
All cottages in Annapolis

Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Annapolis and surrounding area in the past month

See all

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 7 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 25 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 12 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 53 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 25 reviews

Popular with guests booking cottages in Annapolis

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 56,877 reviews

Popular with guests booking cottages in Annapolis

These cottages in Annapolis and nearby have options with free cancellation

See all

Weems Creek Cottage, Annapolis Waterfront

Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 12 reviews

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 25 reviews

Westside Storied

4 Bristol Drive
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

4BR Family Retreat Near Annapolis w Large Yard

Free cancellation options available
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 25 reviews

Fisher House - Downtown Annapolis!

142 Market Street
Free cancellation options available
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 53 reviews

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Traveling by car? These cottages in Annapolis and nearby offer free parking

See all
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 7 reviews
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 25 reviews
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 53 reviews
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 25 reviews
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 56,877 reviews

FAQ about cottages in Annapolis

Cottages That Guests Love in Annapolis

See all
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 11 reviews
The home was completely updated and decorated so cute. It was like a beach cottage. We had everything we needed to cook to include spices and oil. Plenty of extra linens and towels. The neighborhood was extremely quiet and peaceful.
Guest review byBig Mac
Solo traveler