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Annapolis, MD cottages
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25 Cottages at the best price in Annapolis, MD

Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 41 reviews
Annapolis, MD
17/09 – 22/09
£882/nighttotal: £4410 (5 )

Beachfront Home Minutes To Downtown Annapolis Dogs Ok

3 1
cottage, Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay.
The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.
Walk To Everything - Historic Arts District - Annapolis, MD
10 2 reviews
Annapolis, MD
06/11 – 08/11
£425/nighttotal: £850 (2 )

Walk To Everything - Historic Arts District

2 2
cottage, Annapolis
This two-bedroom holiday home in downtown Annapolis offers convenient access to the Maryland Hall for Creative Arts, a 12-minute walk away, and the Maryland State House, a 13-minute walk away, with on-site parking and complimentary Wi-Fi.
This self-catering accommodation accommodates up to six guests and features a fully equipped kitchen, air conditioning, a washer/dryer, and is close to sailing and kayaking opportunities.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 20 reviews
Annapolis, MD
06/11 – 08/11
£577/nighttotal: £1154 (2 )

Secluded Cozy Cottage In Historic Downtown

2 2
cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
The Yellow Cottage On Harness Creek - Annapolis, MD
10 174 reviews
Annapolis, MD
31/07 – 02/08
£285/nighttotal: £570 (2 )

The Yellow Cottage On Harness Creek

2 4
cottage, Annapolis
The Yellow Cottage is located on Harness Creek in Hillsmere, a peaceful residential neighbourhood in Annapolis, just a short distance from Jonas Green State Park and the Smithsonian Environmental Research Center. This charming property has received excellent user ratings, making it a popular choice for travellers.
The cottage offers 88 square metres of living space, comfortably accommodating up to six guests in two bedrooms and a living room with a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as activities such as fishing, crabbing, and kayaking on the creek.
Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games! - Annapolis, MD
10 240 reviews
Annapolis, MD
06/11 – 08/11
£903/nighttotal: £1806 (2 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games!

1 2
cottage, Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.

Our Favourite Family-Friendly Cottages in Annapolis, MD

Family-friendly cottages near the Annapolis, MD coast provide ample space and easy access to local beaches.

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games! - Annapolis, MD
10 240 reviews
Annapolis, MD
06/11 – 08/11
£903/nighttotal: £1806 (2 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games!

1 2
cottage, Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 20 reviews
Annapolis, MD
06/11 – 08/11
£577/nighttotal: £1154 (2 )

Secluded Cozy Cottage In Historic Downtown

2 2
cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 41 reviews
Annapolis, MD
17/09 – 22/09
£882/nighttotal: £4410 (5 )

Beachfront Home Minutes To Downtown Annapolis Dogs Ok

3 1
cottage, Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay.
The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.

Best Annapolis, MD cottages with a garden

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games! - Annapolis, MD
10 240 reviews
Annapolis, MD
06/11 – 08/11
£903/nighttotal: £1806 (2 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games!

1 2
cottage, Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.
The Yellow Cottage On Harness Creek - Annapolis, MD
10 174 reviews
Annapolis, MD
31/07 – 02/08
£285/nighttotal: £570 (2 )

The Yellow Cottage On Harness Creek

2 4
cottage, Annapolis
The Yellow Cottage is located on Harness Creek in Hillsmere, a peaceful residential neighbourhood in Annapolis, just a short distance from Jonas Green State Park and the Smithsonian Environmental Research Center. This charming property has received excellent user ratings, making it a popular choice for travellers.
The cottage offers 88 square metres of living space, comfortably accommodating up to six guests in two bedrooms and a living room with a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as activities such as fishing, crabbing, and kayaking on the creek.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 20 reviews
Annapolis, MD
06/11 – 08/11
£577/nighttotal: £1154 (2 )

Secluded Cozy Cottage In Historic Downtown

2 2
cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 41 reviews
Annapolis, MD
17/09 – 22/09
£882/nighttotal: £4410 (5 )

Beachfront Home Minutes To Downtown Annapolis Dogs Ok

3 1
cottage, Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay.
The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.

Frequently asked questions about cottages in Annapolis, MD

Destinations nearby

Check Out Cottages with a Hot Tub in Annapolis, MD

Settle into a private hot tub at these waterside cottages in Annapolis, MD for the ultimate coastal unwind.

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games! - Annapolis, MD
10 240 reviews
Annapolis, MD
06/11 – 08/11
£903/nighttotal: £1806 (2 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games!

1 2
cottage, Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.

Search Dog-Friendly Holiday Cottages in Annapolis, MD

Secure a dog-friendly cottage in Annapolis, MD featuring outdoor washing stations and proximity to the shoreline.

Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 20 reviews
Annapolis, MD
06/11 – 08/11
£577/nighttotal: £1154 (2 )

Secluded Cozy Cottage In Historic Downtown

2 2
cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 41 reviews
Annapolis, MD
17/09 – 22/09
£882/nighttotal: £4410 (5 )

Beachfront Home Minutes To Downtown Annapolis Dogs Ok

3 1
cottage, Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay.
The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.

Discover Cottages by the Sea in Annapolis, MD

Plan a refreshing maritime trip at comfortable coastal cottages in Annapolis, MD located near the beach.

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games! - Annapolis, MD
10 240 reviews
Annapolis, MD
06/11 – 08/11
£903/nighttotal: £1806 (2 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games!

1 2
cottage, Annapolis

Popular 5-Star Holiday Cottages in Annapolis, MD

Coastal elegance defines our premier luxury cottages in Annapolis, MD, where every detail is considered for your stay.

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games! - Annapolis, MD
10 240 reviews
Annapolis, MD
06/11 – 08/11
£903/nighttotal: £1806 (2 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!<br>great Lodging For Navy Sports Visitors And The Annapolis Blues Games!

1 2
cottage, Annapolis

Choose the Right Cottages with a Pool in Annapolis, MD

These cottages in Annapolis, MD feature swimming pools, perfect for a dip right alongside the local sands.

The Yellow Cottage On Harness Creek - Annapolis, MD
10 174 reviews
Annapolis, MD
31/07 – 02/08
£285/nighttotal: £570 (2 )

The Yellow Cottage On Harness Creek

2 4
cottage, Annapolis

Top Holiday Cottages with Free Parking in Annapolis, MD

Enjoy hassle-free coastal trips with private parking at your cottage in Annapolis, MD, avoiding any extra faff.

Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 41 reviews
Annapolis, MD
17/09 – 22/09
£882/nighttotal: £4410 (5 )

Beachfront Home Minutes To Downtown Annapolis Dogs Ok

3 1
cottage, Annapolis

Explore Holiday Cottages with Spa Facilities in Annapolis, MD

Choose a cottage with a spa in Annapolis, MD for effortless waterside wellness during your coastal break.

Walk To Everything - Historic Arts District - Annapolis, MD
10 2 reviews
Annapolis, MD
06/11 – 08/11
£425/nighttotal: £850 (2 )

Walk To Everything - Historic Arts District

2 2
cottage, Annapolis
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