Search Cottages in Annapolis

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Cottages in Annapolis

A Place To Relax-Side A
Outdoor dining

A Place To Relax-Side A

10.0 out of 10, Exceptional, (24)
"It was an amazing stay would highly recommend and so appreciated our host very pet friendly thank you "
The price is SARĀ 413
SARĀ 794 total
includes taxes & fees
7 Jul - 8 Jul
A Place To Relax-Side A
The Cozy Cottage
Outdoor dining

The Cozy Cottage

10.0 out of 10, Exceptional, (18)
"The cabin was very clean and cozy. The beds were very comfortable. We will be back again. "
The Cozy Cottage
Quaint Little Porch Cottage
Outdoor dining

Quaint Little Porch Cottage

9.8 out of 10, Exceptional, (22)
"We enjoyed our stay, the property is amazing!"
The price is SARĀ 375
SARĀ 682 total
includes taxes & fees
7 Jul - 8 Jul
Quaint Little Porch Cottage
Cozy Belgrade Cottage w/ Wood-Burning Stove!
Fridge, stovetop, dishwasher, coffee/tea maker

Cozy Belgrade Cottage w/ Wood-Burning Stove!

10.0 out of 10, Exceptional, (1)
"Nice location, very quiet and peaceful. Kim was kind enough to let us check in very early! We mostly relaxed and had a great time playing with the ping pong table downstairs."
Cozy Belgrade Cottage w/ Wood-Burning Stove!
Serene Belgrade Hideaway With Fire Pit & Grill!
House (1 Bedroom) | Interior

Serene Belgrade Hideaway With Fire Pit & Grill!

3.0 star property
Serene Belgrade Hideaway With Fire Pit & Grill!
Inviting Des Arc Cabin w/ Fire Pit + Deck!
Terrace/patio

Inviting Des Arc Cabin w/ Fire Pit + Deck!

3.0 star property
Inviting Des Arc Cabin w/ Fire Pit + Deck!
'turtle Rock' - Ironton Cabin w/ Furnished Patio!
House (1 Bedroom) | Interior

'turtle Rock' - Ironton Cabin w/ Furnished Patio!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Stroller, pack n play and high chair. This was amazing "
'turtle Rock' - Ironton Cabin w/ Furnished Patio!
Panther Den Cabin is located 4 miles from Hwy K Campground
1 bedroom, free WiFi, bed sheets

Panther Den Cabin is located 4 miles from Hwy K Campground

9.4 out of 10, Exceptional, (12)
"Nice, clean place to stay with excellent furnished kitchen!"
Panther Den Cabin is located 4 miles from Hwy K Campground
Rustic Caledonia Cabin Near State Parks & Boating!
Exterior

Rustic Caledonia Cabin Near State Parks & Boating!

3.0 star property
Rustic Caledonia Cabin Near State Parks & Boating!
Spacious & Secluded Shook Home w/ Private Hot Tub!
Interior

Spacious & Secluded Shook Home w/ Private Hot Tub!

3.0 star property
Spacious & Secluded Shook Home w/ Private Hot Tub!
Cozy Ironton Cabin w/ Shared Pool & Private Patio!
House (1 Bedroom) | Interior

Cozy Ironton Cabin w/ Shared Pool & Private Patio!

3.0 star property
Cozy Ironton Cabin w/ Shared Pool & Private Patio!
Cozy Belgrade Cottage w/ Wood-burning Stove!
Cottage (2 Bedrooms) | Private kitchen | Oven, stovetop, dishwasher, cookware/dishes/utensils

Cozy Belgrade Cottage w/ Wood-burning Stove!

3.0 star property
Cozy Belgrade Cottage w/ Wood-burning Stove!
Arcadia Valley Bungalows
Exterior

Arcadia Valley Bungalows

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautifully rehabbed old building. The bungalow was a perfect fit for our family. It was equipped with everything we could possibly need and the quirks of an old building make this place charming. It was nicely decorated and clean. The owners were very accommodating and go to great lengths to make sure you are comfortable. The restarunt was fantastic and reasonably priced. Can't wait to come back when the pool is done. Definitely felt like home away from home."
Arcadia Valley Bungalows
Quiet Caledonia Cabin: 18 Mi to Council Bluff Lake
Exterior

Quiet Caledonia Cabin: 18 Mi to Council Bluff Lake

3.0 star property
Quiet Caledonia Cabin: 18 Mi to Council Bluff Lake
Cozy Caledonia Cabin ~ 10 Mi to Elephant Rocks!
Interior

Cozy Caledonia Cabin ~ 10 Mi to Elephant Rocks!

3.0 star property
Cozy Caledonia Cabin ~ 10 Mi to Elephant Rocks!
Walk to Dtwn: Ironton Home in Historic District
House (2 Bedrooms) | Front of property

Walk to Dtwn: Ironton Home in Historic District

3.0 star property
Walk to Dtwn: Ironton Home in Historic District
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Annapolis with Expedia?
Expedia has some wonderful cottages in Annapolis, so get ready for an unforgettable stay on nature's doorstep. If you have a set budget, click on how much you'd like to spend and your preferred property star rating. Or, make the most of our filters to search for cottages with a pool or a hot tub. We'll help you find the perfect place whatever your plans or style of travel.
How can I find cheap cottages in Annapolis?
The quickest way to locate cheap cottages in Annapolis is with Expedia's filter tool. Narrow down your search by amenities, star rating and budget to access awesome bargains in a few clicks.