Severn River Rentals
From $698 per night (USD)VRBO
3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Close to US Naval Academy (1.6 mi.), Navy-Marine Corps Memorial Stadium (1.1mi), and Anne Arundel Medical Center (less t ...
From $698 per night (USD)VRBO
From $303 per night (USD)Expedia
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our 2BR, 1BA Boutique Brick Beauty located in historic Eastport. This beauty is steps from downtown, the U.S ...
From $303 per night (USD)Expedia
From $597 per night (USD)VRBO
Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Perfect home for families traveling to Annapolis! Your family will be close to everything when you stay at this central ...
From $597 per night (USD)VRBO
From $255 per night (USD)VRBO
Waterfront 2-bedroom condo in Eastport, Annapolis with private parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located just half a block from Spa Creek Draw Bridge, this first-floor condo offers water views and a relaxed, upscale a ...
From $255 per night (USD)VRBO
From $978 per night (USD)VRBO
Annapolis Halloween Escape!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Come visit The GOAT Getaway...... • walk to Navy Memorial Stadium - less than 1/2 mile • short 1 1/2 mile drive or walk ...
From $978 per night (USD)VRBO
From $673 per night (USD)Expedia
Boutique Historic Cedar Home 2 blocks from the Waterfront, USNA and Main Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Step into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this pr ...
From $673 per night (USD)Expedia
From $896 per night (USD)VRBO
Steps from the Waterfront with Private Backyard at Historic Philip Clayton House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Historic Philip Clayton House – Downtown Annapolis Retreat Step into Annapolis history at the Philip Clayton House, a l ...
From $896 per night (USD)VRBO
From $1396 per night (USD)Expedia
3-bedroom boat in amazing Annapolis with AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a soothing stay on this boat in Annapolis. This superb 3-bedroom boat features 3 queen beds, heating, and AC. Each ...
From $1396 per night (USD)Expedia
From $562 per night (USD)VRBO
Newly Renovated Eastport Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located in Annapolis, this lovely house features 2 queen bedrooms, 2 bathrooms with showers, and a cozy living room with ...
From $562 per night (USD)VRBO
From $399 per night (USD)Expedia
Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Boat show vendors and visitors!!! This quiet waterfront Annapolis apartment features a queen bed, double futon, Full ki ...
From $399 per night (USD)Expedia
From $762 per night (USD)VRBO
Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Eastport Cape Cod – Walk to Downtown Annapolis Welcome to your Annapolis retreat! This all-new Cape Cod in the heart of ...
From $762 per night (USD)VRBO
From $677 per night (USD)Expedia
Historic Annapolis Retreat – Steps from the Statehouse & City Dock with Parking and Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
In the shade of the Maryland Statehouse, this historic home has welcomed family, friends, and travelers for more than 17 ...
From $677 per night (USD)Expedia
From $353 per night (USD)VRBO
Pet Friendly Annapolis Stay Walk to DTA & Stadium
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Enjoy the best of Annapolis from this centrally located, pet-friendly home. Walk to Downtown Annapolis, Navy ta ...
From $353 per night (USD)VRBO
From $320 per night (USD)VRBO
1 Block to USNA Stadium: Modern Annapolis Home!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Central Location | New Build | In-Unit Laundry | Fire Pit | 2 Mi to USNA Settle into this Annapolis vacation rental tha ...
From $320 per night (USD)VRBO
From $285 per night (USD)VRBO
Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Quiet furnished, double bed, kitchenette, private full bathroom quiet and private studio in home 10 minutes from Downto ...
From $285 per night (USD)VRBO
From $380 per night (USD)Expedia
Eastport Private Suite – 1 mi to USNA & Downtown, Near Boat Shows & Comm Week
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Goat House, a secure and modern private suite in Eastport, just 1 mile from the U.S. Naval Academy and mi ...
From $380 per night (USD)Expedia
From $509 per night (USD)VRBO
Waterfront Condo with Views of Annapolis, Pool & Prime Eastport Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Wake up to sparkling water views and the charm of historic Annapolis right outside your window. This 3rd-floor waterfron ...
From $509 per night (USD)VRBO
From $655 per night (USD)Expedia
Fabulous 5-bedroom house with AC in charming Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Looking to explore Annapolis and live comfortably on a budget? This cozy square house will be just right for you! The si ...
From $655 per night (USD)Expedia
From $1142 per night (USD)VRBO
Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Your Fun Filled getaway awaits in Annapolis at this Phenomenal Waterfront House with Hot Tub! With 5 bedrooms including ...
From $1142 per night (USD)VRBO
From $288 per night (USD)Expedia
The Red Door Cottage in Eastport - Pet-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This stylish, pet-friendly boho retreat is just 1 mile from downtown Annapolis and Eastport’s restaurants—your perfect h ...
From $288 per night (USD)Expedia
From $378 per night (USD)VRBO
Modern Gem Near Historic Annapolis & Naval Academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Built in August 2025 | Group-Friendly Layout w/ 4 En-Suite Bedrooms | 1 Mi to Shopping, Dining & Hospitals Spacious and ...
From $378 per night (USD)VRBO