Annapolis Rentals
From $331 per night (USD)VRBO
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, ...
From $331 per night (USD)VRBO
From $389 per night (USD)Expedia
Downtown Pinkney House w/Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to ...
From $389 per night (USD)Expedia
From $593 per night (USD)VRBO
Historic Annapolis Home!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
🌟 Discover the Allure of Historic Annapolis Living! 🌟 Welcome to your captivating 2-bedroom, 1.5-bath home nestled in ...
From $593 per night (USD)VRBO
From $235 per night (USD)VRBO
Maryland Inn 2 Double Beds, Historic Inns, Modern Amenities, Event Space, City Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $235 per night (USD)VRBO
From $215 per night (USD)VRBO
Enjoy Stepping Back in Time at Charming Hotel in Annapolis - Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $215 per night (USD)VRBO
From $449 per night (USD)VRBO
2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $449 per night (USD)VRBO
From $223 per night (USD)VRBO
Authentic 18th Century Hotel Near US Naval Academy - Walking Distance
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $223 per night (USD)VRBO
From $393 per night (USD)VRBO
Maryland Inn 2 Doubles, Pet-Friendly, 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $393 per night (USD)VRBO
From $404 per night (USD)VRBO
2 Maryland Inn 2DBeds, Historic Inns of Annapolis, Waterfront Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $404 per night (USD)VRBO
From $226 per night (USD)VRBO
Elegant Stay Perfect for Romantic Getaway, Just Steps from Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $226 per night (USD)VRBO
From $193 per night (USD)VRBO
Unique Victorian Stay w/ Modern Amenities + Steps from Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $193 per night (USD)VRBO
From $511 per night (USD)VRBO
Robert Johnson Townhouse, Historic Inns, Fireplace, Downtown Locale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $511 per night (USD)VRBO
From $245 per night (USD)VRBO
Governor Calvert 2 Double Beds, Historic Inns, Gym Access, Near Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $245 per night (USD)VRBO
From $203 per night (USD)VRBO
Maryland Inn King, Historic Inns, Fireplace, Elegant Dining, Waterfront Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $203 per night (USD)VRBO
From $212 per night (USD)VRBO
Robert Johnson 2 Double Beds, Historic Inns, Antique Style, Near Chesapeake Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $212 per night (USD)VRBO
From $450 per night (USD)VRBO
Elegant Stay Perfect for Exploring Annapolis' Shops and Boutiques.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $450 per night (USD)VRBO
From $204 per night (USD)VRBO
Robert Johnson King, Historic Inns, Near Top Dining & City Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $204 per night (USD)VRBO
From $212 per night (USD)VRBO
Charming Downtown Hotel w/ Vintage Character + Modern Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $212 per night (USD)VRBO
From $219 per night (USD)VRBO
Elegant Boutique Hotel Near Maryland State House - Short Walk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $219 per night (USD)VRBO
From $356 per night (USD)VRBO
2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $356 per night (USD)VRBO
From $998 per night (USD)VRBO
Stunning Home Nestled on the Peninsula of Eastport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom Annapolis home is an absolute gem, especially with off-street parking! The Craftsman style architecture a ...
From $998 per night (USD)VRBO
From $300 per night (USD)Expedia
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorat ...
From $300 per night (USD)Expedia
From $157 per night (USD)VRBO
Experience Historical Annapolis + Complimentary Breakfast! Outdoor Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $157 per night (USD)VRBO
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Gorgeous House in the Heart of Annapolis, Walk to Everything!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located within walking distance of everything Annapolis has to offer, this 3BR/2.5 Bath historic Craftsman home is beaut ...
Click For PricingExpedia
From $1378 per night (USD)VRBO
Eastport Classic Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to our Eastport home where hardwood floors, large windows that allow ample natural light, and a cozy fi ...
From $1378 per night (USD)VRBO
From $461 per night (USD)Expedia
Walk to Everything - Historic Art’s District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
HISTORIC ANNAPOLIS/ART’S DISTRICT Built in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill ...
From $461 per night (USD)Expedia
From $574 per night (USD)VRBO
Mins to Downtown in Waterfront community at Pet-friendly Pinecrest Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Just minutes from Downtown Annapolis, this charming Cape is located in a quiet water-privileged neighborhood with easy a ...
From $574 per night (USD)VRBO
From $979 per night (USD)Expedia
On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Historic Charm Across from the Naval Academy Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-ba ...
From $979 per night (USD)Expedia
From $201 per night (USD)VRBO
Governor Calvert King, Historic Inns, Four-Poster Bed, Dining, Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $201 per night (USD)VRBO
From $492 per night (USD)Expedia
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Still available for Commissioning Week 2025! This beautifully-restored 1 bedroom apartment is on the lower level of a 2 ...
From $492 per night (USD)Expedia
From $1444 per night (USD)VRBO
Spacious Converted Carriage House in Historic District near USNA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in this updated and sophisticated house near the USNA in Annapolis with the largest garden in downtown. This tranq ...
From $1444 per night (USD)VRBO
From $530 per night (USD)Expedia
Stay in Historic apartment 2 blocks from Main St with parking - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Still available for Commissioning Week 2025! Stay right in the heart of Historic Annapolis, just 2 blocks from Main Str ...
From $530 per night (USD)Expedia
From $328 per night (USD)VRBO
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
In the heart of Annapolis, where the bay breeze blows, Stands a small cottage, the Captain's Quarters, a peaceful repos ...
From $328 per night (USD)VRBO
From $456 per night (USD)Expedia
Stay in the heart of Historic Annapolis 2 blocks from Main Street - dog friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Still available for Commissioning Week 2025! Inquire about discounted extended stays! Stay right in the heart of Hist ...
From $456 per night (USD)Expedia
From $943 per night (USD)VRBO
Magnolia Harbor Retreat - 4 BR/3BA HISTORIC DOWNTOWN ANNAPOLIS- QUIET STREET
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RENT-001081-2024 - HOME OWNER HAS A PET SO THIS SHOULD BE TAKEN INTO CONSIDERATION WHEN BOOKING BY ANY GUEST WITH ALLERG ...
From $943 per night (USD)VRBO
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Spend Commissioning Week Here: Walk to Yard, Pool, Hot Tub, Kayaks, and more...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Park once and walk everywhere! Plus, enjoy our pool, hot tub, fire pit and large patio for your gatherings. Have your mo ...
Click For PricingExpedia
From $303 per night (USD)VRBO
Minutes from History: 2 Relaxing Units w/ Free Breakfast Near Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $303 per night (USD)VRBO
From $306 per night (USD)VRBO
Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $306 per night (USD)VRBO
From $399 per night (USD)VRBO
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this delightful 3-bedroom Annapolis retreat. With a king bed, queen bed, and full bed, this hou ...
From $399 per night (USD)VRBO
From $1276 per night (USD)Expedia
Beautiful 7BR home minutes from downtown Annapolis
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 14
Newly renovated modern colonial on several acres just minutes from downtown Annapolis and the Naval Academy. Chefs kitch ...
From $1276 per night (USD)Expedia
From $683 per night (USD)VRBO
Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful house on a quiet street two blocks from the Navy Stadium with easy access to downtown Annapolis via the stadium ...
From $683 per night (USD)VRBO
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Amazing townhome in Annapolis, near Restaurants, USNA, Shopping centers, & more
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 3
Amazing three bedroom townhome with Masters suite(with full bathroom), and 2 additional bedrooms with access to one full ...
Click For PricingExpedia
Click For PricingVRBO
Waterviews, steps to restaurants and downtown from First Mate
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Still available for Commissioning Week 2025! Stunning 4 Bedroom / 3.5 Bath Home in Eastport with Water Views and Expans ...
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From $275 per night (USD)Expedia
Adorable 1 bedroom apartment in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Enjoy a stylish experience at this centrally-located apartment. 2 minute walk to Main Street and all of the att ...
From $275 per night (USD)Expedia
From $373 per night (USD)VRBO
2 Bedroom Renovated Condo in Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Newly renovated 2 bedroom apartment in downtown Annapolis. Steps from Main Street and all that Annapolis has to ...
From $373 per night (USD)VRBO
From $592 per night (USD)VRBO
Downtown Annapolis Gem: 3BR/2BA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to our newly renovated 3BR/2BA apartment in downtown Annapolis! With two king beds, one queen bed, and ...
From $592 per night (USD)VRBO
From $238 per night (USD)VRBO
1 room with additional amazing sunroom
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 3
Summary: Enjoy a wonderful experience at this centrally-located apartment. 2 minute walk to Main Street and all of the a ...
From $238 per night (USD)VRBO
From $234 per night (USD)Expedia
Lovely 1 bedroom apartment in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Summary: Keep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to off ...
From $234 per night (USD)Expedia
From $623 per night (USD)VRBO
Mins to DTA - King Beds - Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gat ...
From $623 per night (USD)VRBO
From $314 per night (USD)VRBO
2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Consider this charming cottage your home away from home while you visit Annapolis. Located on Cove of Cork, adjacent to ...
From $314 per night (USD)VRBO
From $1434 per night (USD)VRBO
Downtown Annapolis Duke's House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: This newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Anna ...
From $1434 per night (USD)VRBO
From $886 per night (USD)VRBO
Main Street 4BR Gem – Steps to Waterfront, USNA, Shops & Dining
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Above it All - Downtown Historic Annapolis Vacation Rental on Main Street - PLEASE NOTE: THIS PROPERTY IS MANAGED BY AN ...
From $886 per night (USD)VRBO
From $792 per night (USD)VRBO
Townhome steps from Main St. with private backyard patio & parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
From $792 per night (USD)VRBO
From $478 per night (USD)Expedia
Five Star Charmer! Great Location Downtown & Stadium! Parking too!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
New to the market and just in time for Navy Football. Located at the five star Corner House. Conveniently located on th ...
From $478 per night (USD)Expedia
From $969 per night (USD)VRBO
Perfect Townhouse for USNA Commissioning Week!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to the perfect townhouse for USNA Commissioning Week! As a former midshipman, I know how important it is to have ...
From $969 per night (USD)VRBO
From $570 per night (USD)Expedia
Steps From Marinas and Restaurants & Private Backyard at Eastport Third Time's the Charm
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Still available for Commissioning Week 2025! Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Histor ...
From $570 per night (USD)Expedia
From $336 per night (USD)VRBO
Naval Academy Gate 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommod ...
From $336 per night (USD)VRBO
From $484 per night (USD)Expedia
Spacious home in historic Annapolis, near USNA
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Annapolis, enjoy what this 3-bedroom house has to offer. With 2 queen beds and 2 twin bed, guests can relax i ...
From $484 per night (USD)Expedia
From $536 per night (USD)VRBO
Charming on Charles
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our elegant stand alone charming home on Charles Street in Historic Annapolis . This 3 bedroom 2.5 bath is ju ...
From $536 per night (USD)VRBO
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Annapolis Home Near Beach & Quiet Waters Park!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
2,552 Sq Ft | Dog Friendly w/ Fee | Wood-Burning Fireplace | 4 Mi to Downtown Annapolis Nestled just 2 miles from the C ...
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From $1028 per night (USD)VRBO
Historic Annapolis Treasure
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Entire Home in Historic Downtown Annapolis Forget your worries in this spacious and serene enchanting Victorian home in ...
From $1028 per night (USD)VRBO
From $495 per night (USD)Expedia
Walking distance to Navy Stadium! No cleaning fees!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This centrally located 3-story rental is steps away from everything Annapolis offers! Whether you're in town to explore ...
From $495 per night (USD)Expedia
From $114 per night (USD)VRBO
Waterfront condo in Eastport, ONLY available for the Legislative session
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
On Back Creek in Eastport, this delightful condo offers 2 bedrooms - one with a king bed and the other with a cozy murph ...
From $114 per night (USD)VRBO
From $548 per night (USD)VRBO
Darling on Dean Street- Nautical home w parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Ideally located between the vibrant West Street and the historic Main Street, our downtown Annapolis home offers easy ac ...
From $548 per night (USD)VRBO
From $604 per night (USD)VRBO
Charming 4-bedroom house 2 blocks from the Navel Academy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 4-bedroom house in Annapolis is perfect for your escape to relaxation. With 4 queen beds and 3 bathrooms equipped w ...
From $604 per night (USD)VRBO
From $511 per night (USD)Expedia
Marymont Cottage in awesome Annapolis walking distance to local pub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this adorable 3-bedroom gem in Annapolis, just across the creek from sought after West Annapolis. This charming ...
From $511 per night (USD)Expedia
From $381 per night (USD)VRBO
Cozy apartment in Historic Annapolis with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Annapolis apartment is located within walking distance of everything Annapolis has to offer. Located just outside ...
From $381 per night (USD)VRBO
From $362 per night (USD)Expedia
Newly Renovated Downtown Annapolis Charm - Game Room, Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Home in the Historic District! You will be in the heart of downtown Annapolis. Walk to USNA, St. John's College, the St ...
From $362 per night (USD)Expedia
From $988 per night (USD)VRBO
Naptown Villa House S
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Welcome to the Naptown Villa house! This fully-renovated home located in downtown Annapolis has all the thought ...
From $988 per night (USD)VRBO
From $736 per night (USD)Expedia
Admiral's Abode Abode
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 4-bedroom, 3-bath home in the heart of downtown Annapolis! This beautifully updated property is steps from the ...
From $736 per night (USD)Expedia
From $592 per night (USD)VRBO
Elegant & Bright Historic Home 3BR\/2,5BA, 2 kings, 1 queen, 5 min to USNA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek ...
From $592 per night (USD)VRBO
From $683 per night (USD)Expedia
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 15
Summary: This charming 5 BR (3x true bedrooms and 2x basement rooms with bunk beds) home is conveniently located in Anna ...
From $683 per night (USD)Expedia
From $611 per night (USD)VRBO
Charming Historic Row House in The Heart of Eastport's Horn Point
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this stunning historic rowhouse located in the charming and highly sought-after neighborhood of Horn Point Ea ...
From $611 per night (USD)VRBO
From $305 per night (USD)VRBO
Charming 2-bedroom apartment with WiFi, AC, kitchen, wash/dryer in Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Unwind in Annapolis at this charming 2 bedroom apartment. Master bedroom includes a queen bed and second smaller fits a ...
From $305 per night (USD)VRBO
Click For PricingVRBO
Downtown Nights on the Water - Classic Cruiser Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the heart of Annapolis, this 35-foot Formula boat offers an unforgettable overnight stay. With a small kitche ...
Click For PricingVRBO
From $705 per night (USD)Expedia
NEW! Cozy Coastal Retreat in the Heart of Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this charming 3-bedroom, 2-bathroom townhouse, ideally located in the serene community of Eastport in Annapol ...
From $705 per night (USD)Expedia
From $832 per night (USD)VRBO
New! All Star Annapolis Retreat - Walk to Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to our Town- House in Annapolis Maryland. This charming 1.5-story retreat offers 2,400 square feet of ...
From $832 per night (USD)VRBO
From $546 per night (USD)Expedia
Newly renovated in DTA w parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom, 2.5-bath single-family home mixes modern renovations with 1896 classic charm. It's been decorated with u ...
From $546 per night (USD)Expedia
From $704 per night (USD)VRBO
Less than 1 mile to Navy Stadium, fenced-in yard and dog-friendly home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Still Available for Commissioning Week 2025! A new home but managed by experienced hosts, iTrip Annapolis, dedicated to ...
From $704 per night (USD)VRBO
From $517 per night (USD)Expedia
Stay in the heart of Annapolis on King George Street steps to Gate 1 & Main Street
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Historic Annapolis Retreat! Discover this newly-renovated and professionally-decorated gem on the presti ...
From $517 per night (USD)Expedia
From $1199 per night (USD)VRBO
New luxury home in Downtown Annapolis with parking & multiple outdoor spaces
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this beautifully remodeled, professionally designed home in the family-friendly Murray Hill neighborhood of A ...
From $1199 per night (USD)VRBO
From $545 per night (USD)Expedia
Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
ALL NEW! Just minutes from USNA Stadium, downtown Annapolis and US Naval Academy, MBA Homes' Nautical Oasis is perfect f ...
From $545 per night (USD)Expedia
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Efficiency Apartment Close to Annapolis. .
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Furnished efficiency apartment in Annapolis, close to downtown area, and easy access to Highways. Private Entrance, pri ...
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From $1412 per night (USD)VRBO
Waterfront Oasis with pool! 4 BR home minutes from downtown Annapolis!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1412 per night (USD)VRBO
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Unique 2-Bedroom Condo in Renovated Church Parish House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into a truly exceptional condo nestled in a beautifully preserved historic church, just two blocks from the U.S. Na ...
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From $1112 per night (USD)Expedia
Available for Commissioning Week and Boat shows. Heated Pool and great backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay comfortably in my home in Annapolis at this 3-bedroom house. With a king bed, queen bed, and two cozy sofa beds, t ...
From $1112 per night (USD)Expedia
From $484 per night (USD)VRBO
Boat-N-Breakfast! Luxurious Accommodations Aboard a 44' Catamaran
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The most fun way to visit America's Sailing Capital, on the water accommodations aboard the sailcat Zep Tepi! Our cata ...
From $484 per night (USD)VRBO
From $431 per night (USD)Expedia
Annapolis Blue and Gold Haven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Nestled in the heart of Annapolis, this charming 2-bedroom townhome offers the perfect blend of comfort and con ...
From $431 per night (USD)Expedia
From $316 per night (USD)VRBO
Cozy 2-bedroom home with WiFi and huge backyard minutes from downtown Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Annapolis, this delightful house is a dream. With 2 cozy bedrooms, heating, AC, WiFi, and a washing machine, ...
From $316 per night (USD)VRBO
From $233 per night (USD)VRBO
\"The Studio\" Apartment in Colonial Historic District, Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...
From $233 per night (USD)VRBO
From $367 per night (USD)VRBO
\"The Flat\" Apartment in Colonial Historic District, Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...
From $367 per night (USD)VRBO
From $380 per night (USD)VRBO
The Penthouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...
From $380 per night (USD)VRBO
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Charming Historic 3-bedroom Estate in Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Lynder's Luxury Lodging-Annapolis. Discover this 3-bedroom Colonial gem in the heart of Downtown Annapolis ( ...
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From $361 per night (USD)Expedia
Charming apt in the heart of Eastport & Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Start your Annapolis adventure in this charming 1-bedroom apartment, comfortably accommodating up to 7 guests. Located i ...
From $361 per night (USD)Expedia
From $345 per night (USD)VRBO
Robert Johnson Queen at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $345 per night (USD)VRBO
From $310 per night (USD)VRBO
Explore Local Attractions, Just Across Maryland State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $310 per night (USD)VRBO
From $831 per night (USD)VRBO
Robert Johnson Suite at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $831 per night (USD)VRBO
From $602 per night (USD)VRBO
Experience History in Annapolis, Near Chesapeake Bay & Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $602 per night (USD)VRBO
From $350 per night (USD)VRBO
Worry-free Stay, Allergy-friendly Room, Exceeds HEPA Standards
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $350 per night (USD)VRBO
From $342 per night (USD)VRBO
Robert Johnson 2 Double Beds Pure Wellness Room at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $342 per night (USD)VRBO