Hidden Wine Cellar Eastport Retreat

6 guests · 2 bedrooms · 1 bath

This House in Annapolis, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Pet-Friendly Eastport Yard & Fire Pit

6 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Garden

Business stays, family stays, couples stay, getaway vacation, and rental in Annapolis at Pet-Friendly Eastport Yard & Fire Pit for $501 for your next trip.

10 / 10

Outstanding(31 Ratings)

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

8 guests · 3 bedrooms · 2 baths

Indulge in a peaceful retreat at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free, our elegant House in Annapolis. Enjoy amenities including Pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

10 / 10

Outstanding(8 Ratings)

Pet-Friendly Eastport | Yard & Fire Pit

6 guests · 2 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Annapolis at Pet-Friendly Eastport | Yard & Fire Pit for $496 for your next trip.

10 / 10

Outstanding(5 Ratings)

Unique and central in Eastport

8 guests · 4 bedrooms · 3 baths

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Annapolis, at $566 per night for your next great vacation.

10 / 10

Outstanding(1 Rating)

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.

12 guests · 4 bedrooms · 2 baths

Looking for a House in Annapolis, this House for $548 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

10 / 10

Outstanding(31 Ratings)

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

8 guests · 3 bedrooms · 2 baths

Looking for a House in Annapolis, this House for $554 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

10 / 10

Outstanding(12 Ratings)

Waterfront 2-Bedroom Condo on Spa Creek

Apartment

6 guests · 2 bedrooms · 1 bath

When traveling to Annapolis, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $510 per night.

10 / 10

Outstanding(5 Ratings)

Unique and central in Eastport

8 guests · 4 bedrooms · 3 baths

This attractive House in Annapolis, $566 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10 / 10

Outstanding(12 Ratings)

Waterfront 2-Bedroom Condo on Spa Creek

Apartment

6 guests · 2 bedrooms · 1 bath

Looking for the perfect place to call home during your trip to Annapolis? This Apartment offers a comfort and style with top-notch amenities, including Pets allowed, Family friendly and Non-smoking, and more.

9.8 / 10

Outstanding(17 Ratings)

Ahoy! Game Room, Screened Porch, Yard Mins to DTA

9 guests · 3 bedrooms · 2 baths

Looking for a House in Annapolis, this House for $584 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

7 / 10

Good(1 Rating)

Unique Eastport Bungalow w Yard

8 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Balcony/Terrace

This House in Annapolis, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

10 / 10

Outstanding(17 Ratings)

Ahoy! Game Room, Screened Porch, Yard Mins to DTA

9 guests · 3 bedrooms · 2 baths

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Annapolis, at $584 per night for your next great vacation.

9.8 / 10

Outstanding(59 Ratings)

Nautical Feel to This Beautiful Eastport Home

6 guests · 2 bedrooms · 2 baths

Experience the best of Annapolis with this House available for $555. This property is equipped with amenities including Pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

10 / 10

Outstanding(17 Ratings)

Historic Annapolis Home | 2 Blocks to Main St

9 guests · 3 bedrooms · 2 baths

This House in Annapolis, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

9.8 / 10

Outstanding(59 Ratings)

Nautical Feel to This Beautiful Eastport Home

6 guests · 2 bedrooms · 2 baths

Looking to create some memories in Annapolis? Look no further than our House, Nautical Feel to This Beautiful Eastport Home. Enjoy top-rated amenities including Pets allowed, Family friendly and Non-smoking, and more.

10 / 10

Outstanding(74 Ratings)

Eastport Historic Firehouse with Parking, Dogs OK

8 guests · 2 bedrooms · 3 baths

This House in Annapolis, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

10 / 10

Outstanding(12 Ratings)

Historic Suite 2 Blocks from Main St with On-Site Parking | Dog-Friendly

Apartment

6 guests · 2 bedrooms · 1 bath

Enjoy the best of Annapolis in our Apartment, Historic Suite 2 Blocks from Main St with On-Site Parking | Dog-Friendly. A stunning property with amenities including Pets allowed, Family friendly and Non-smoking, and more.

9.8 / 10

Outstanding(74 Ratings)

Beautifully Renovated Historic District Home

6 guests · 3 bedrooms · 2 baths

This House for $598 in Annapolis, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

10 / 10

Outstanding(3 Ratings)

Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

6 guests · 2 bedrooms · 1 bath

This inviting House in Annapolis can fit your needs for many types of vacations, at $669 per night.

9.9 / 10

Outstanding(74 Ratings)

Eastport Historic Firehouse with Parking, Dogs OK

8 guests · 2 bedrooms · 3 baths

Looking for a memorable stay in Annapolis? Our House might just be what you're looking for. Enjoy amenities including Pets allowed, Family friendly and Non-smoking, and more during your stay.

9.1 / 10

Outstanding(7 Ratings)

Fisher House - Downtown Annapolis!

9 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Outdoor Cooking

House in Annapolis, for $625 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

10 / 10

Outstanding(44 Ratings)

Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard

7 guests · 2 bedrooms · 1 bath

When traveling to Annapolis, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $565 per night.

You can save with One Key

10 / 10

Outstanding(3 Ratings)

Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

6 guests · 2 bedrooms · 1 bath

Discover the beauty of Annapolis with a stay at Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard, a top rated House with amenities such as Pets allowed, Family friendly and Non-smoking, and more.

10 / 10

Outstanding(44 Ratings)

Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard

7 guests · 2 bedrooms · 1 bath

Are you ready to indulge in a relaxing getaway? Our House in Annapolis has everything you need for a rejuvenating stay. Treat yourself to Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard's exceptional amenities, such as Pets allowed, Family friendly and Non-smoking.

9.4 / 10

Outstanding(22 Ratings)

Secluded Cozy Cottage in Historic Downtown

Cottage

8 guests · 2 bedrooms · 1 bath

Looking for a memorable stay in Annapolis? Our Cottage might just be what you're looking for. Enjoy amenities including Pets allowed, Family friendly and Non-smoking, and more during your stay.

You can save with One Key

9.4 / 10

Outstanding(22 Ratings)

Secluded Cozy Cottage in Historic Downtown

Cottage

8 guests · 2 bedrooms · 1 bath

Nestled in Annapolis, this Cottage is perfect for your next vacation. Enjoy Secluded Cozy Cottage in Historic Downtown's top-rated amenities, including Pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

Historic Row Home in Downtown Annapolis

12 guests · 2 bedrooms · 2 baths

Soak up the beauty of Annapolis in our House, Historic Row Home in Downtown Annapolis. With a range of amenities such as Pets allowed, Family friendly and Non-smoking, you'll feel right at home.

Historic Row Home in Downtown Annapolis

12 guests · 2 bedrooms · 2 baths

Experience vacation in Annapolis with our House, Historic Row Home in Downtown Annapolis. Enjoy amenities such as Pets allowed, Family friendly and Non-smoking, and more.

10 / 10

Outstanding(6 Ratings)

Historic Annapolis Retreat – Steps from the Statehouse & City Dock with Parking and Private Patio

8 guests · 3 bedrooms · 2 baths

Experience the best of Annapolis with this House available for $595. This property is equipped with amenities including Pets allowed, Family friendly and Non-smoking, and more.