Severn River Rentals
- From $460 per night (USD)
VRBO
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a beautiful house for your stay in Annapolis! This large fully renovated house is just off West Street, 1.5 mil ...
From $460 per night (USD)VRBO
- From $471 per night (USD)
Expedia
Historic happy home, steps to Main Street, parking and lots of outdoor space
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...
From $471 per night (USD)Expedia
- Click For Pricing
VRBO
Fully renovated house in the heart of the Historic District!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully updated 3 bed/1.5 bath in Historic Annapolis, less than a mile from the main gates of the Naval Academy! Main bedr ...
Click For PricingVRBO
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Expedia
Private Eastport Guest Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a clean, comfortable and private suite in the heart of Eastport. Steps away from Davis' Pub and Forward Brewing as ...
Click For PricingExpedia
- From $813 per night (USD)
VRBO
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
A perfect harmony of classic and modern, this newly renovated property has a quintessential Annapolis feel. Nestled in t ...
From $813 per night (USD)VRBO
- From $423 per night (USD)
Expedia
Available 2024 Commissioning Week 20 mins to USNA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**Still available for 2024 Commissioning Week** Enjoy the magnificent waterfront views from this custom-built home with ...
From $423 per night (USD)Expedia
- Click For Pricing
Expedia
Newly-renovated waterfront home with private pier and all the bells and whistles
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Stay in this exceptional newly-renovated waterfront home with phenomenal views of the Severn River. Nestled in the desir ...
Click For PricingExpedia
- From $170 per night (USD)
VRBO
Cozy Bungalow w\/ Ample Outdoor Space Near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to my charming Annapolis home in Eastport! My cozy 1 bed/1 bath house features a versatile spare room perfect fo ...
From $170 per night (USD)VRBO
- Click For Pricing
VRBO
USNA Commissioning Week - 2 Blocks Away
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
Click For PricingVRBO
- From $833 per night (USD)
VRBO
The place to be together! Linstead on the Severn River
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Two main floor bedrooms& baths and three bedrooms and one bath upstairs. Open and meandering decorator’s home full of en ...
From $833 per night (USD)VRBO
- From $785 per night (USD)
VRBO
Elegant waterfront cottage and guest house, garden setting, clubhouse and beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy waterfront views from every window, crabbing from the pier, sundowners on the wrap around porch, set in a private ...
From $785 per night (USD)VRBO
- From $404 per night (USD)
VRBO
Cozy private home 3 min walk to downtown, elevator, private driveway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a short walk to the center of Annapolis and harbor, this home includes a private driveway for 1 large vehicle (a r ...
From $404 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Perfect Eastport Location, walk everywhere, Annapolis NO CLEANING FEE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Leave your car behind and walk to everything Annapolis, Eastport is full of charm, Restaurants, Museums, live music. Com ...
From $299 per night (USD)VRBO
- From $406 per night (USD)
Expedia
Gracie's Garden in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come stay in a Heavenly Bed in the heart of Annapolis. Located 1 mile from downtown this garden apartment is completely ...
From $406 per night (USD)Expedia
- From $675 per night (USD)
VRBO
Parking at Stunning On Cloud 9 with private patio pet-friendly
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this stunning home in downtown Annapolis with all the things you will ever need: parking for 2 cars (1 on-sit ...
From $675 per night (USD)VRBO
- From $788 per night (USD)
Expedia
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*Still available for 2024 Commissioning Week - 5-night minimum! Watch the sunrise on the private beach at Oh Happy Bay. ...
From $788 per night (USD)Expedia
- From $822 per night (USD)
VRBO
Unique Listing! Entire Downtown Triplex w\/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $822 per night (USD)VRBO
- From $715 per night (USD)
Expedia
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $715 per night (USD)Expedia
- From $695 per night (USD)
VRBO
BY THE BAY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer. Our home is located jus ...
From $695 per night (USD)VRBO
- From $786 per night (USD)
VRBO
BAY RIDGE MODERN HOME WITH VINTAGE CHARM
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful spacious modern family home with vintage charm. A great gathering spot for family or just wanting to spend som ...
From $786 per night (USD)VRBO
- From $580 per night (USD)
VRBO
Perfect Beautiful 6 Bedroom 4 bathroom Gem in Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Enjoy a Beautiful 6 Bedroom, 4 bathroom home in the capital of Maryland, centrally-located in the heart of Annapolis. Mi ...
From $580 per night (USD)VRBO
- From $466 per night (USD)
VRBO
3 bdrm close to city center, great yard & parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Approx .7 mile to stadium, 1.4 to Naval Academy. Walk to free shuttle at Park Place and to great coffee every morning fr ...
From $466 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Historic house in Annapolis Arts District
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Super host house rental in charming historic house, private and upscale, tucked away in the quiet President’s Hill neigh ...
From $250 per night (USD)VRBO
- From $179 per night (USD)
Expedia
Charming 18th Cent. Home in Historic Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lower level furnished apartment, in one of Historic Annapolis's 10 oldest Private residences. Lovely wood, brick & ornam ...
From $179 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Secluded Cozy Cottage in Historic Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy having Historic Ann ...
From $400 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Comfortable Townhouse Minutes from City Dock and US Naval Academy!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Make this well-appointed townhouse your home away from home in the family-friendly Hunt Meadow community conveniently lo ...
From $300 per night (USD)VRBO
- From $449 per night (USD)
VRBO
Historic 3 Bedroom Downtown Annapolis Townhome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, ...
From $449 per night (USD)VRBO
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Expedia
Parking! Modern Cozy Home by DTA, Navy Stadium, and AAMC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Make yourself at home at our midcentury modern escape located right in the heart of Annapolis! This 2 bedroom 2.5 bathro ...
Click For PricingExpedia
- From $385 per night (USD)
VRBO
Modern and cozy Captain’s Crossing Cape house in West Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this mid-century modern, Cape Cod in West Annapolis. This "Ralph-Lauren Cottage" exudes that "Annapolitan fee ...
From $385 per night (USD)VRBO
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Expedia
Peaceful Home in Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Relax with the whole family at this peaceful place to stay. A quaint 4-bedroom home tucked away on 2.2 acres. Enjoy the ...
Click For PricingExpedia
- From $120 per night (USD)
VRBO
Modern Coastal Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Welcome to our newly renovated home in t ...
From $120 per night (USD)VRBO
- Click For Pricing
Expedia
Hyde Park Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Cute house at the end of a cul-de-sac in a friendly neighborhood! The house has two bedrooms and two full baths. It can ...
Click For PricingExpedia
- From $467 per night (USD)
VRBO
Fantastic Location In DTA with its own Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our favorite part about this home is its location in DTA with parking. We can walk to all the restaurants, pubs, USNA, ...
From $467 per night (USD)VRBO
- From $455 per night (USD)
VRBO
Charming Home located minutes from the Naval Academy and Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Private 4BR, 2.5BA luxurious Gem was recently upgraded, and tastefully decorated awaits your arrival. The ranch style ho ...
From $455 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Serene waterfront home with kayaks, paddle board, grill, firepit, W\/D, and AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Valentine Creek Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $295 per night (USD)VRBO
- From $389 per night (USD)
Expedia
Walk to Main Street from Waterfront Condo with pool and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
This beautifully-renovated and designed 2-bedroom/2-bath condo feels like a luxury hotel suite with views of Spa Creek a ...
From $389 per night (USD)Expedia
- From $410 per night (USD)
VRBO
History & Charm Near the Annapolis City Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the he ...
From $410 per night (USD)VRBO
- From $400 per night (USD)
VRBO
4 Bedroom - Completely updated. Super safe neighborhood close to USNA stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Not your typical Airbnb. This is our vacation house too and we have it stocked so you can enjoy all of the amenities of ...
From $400 per night (USD)VRBO
- From $420 per night (USD)
VRBO
Luxe Houseboat: Breathtaking Skyline 360 Views
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
| OVERVIEW | Welcome to FLOHOM 1 | Bay Escape, your home away from shore! Our luxury houseboat is docked at the premie ...
From $420 per night (USD)VRBO
- From $264 per night (USD)
Expedia
3 Story Stunner in Murray Hill <1 mile from USNA!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Summary: This is an *amazing* 3 story / 5 bedroom house with a finished basement! This is the perfect house for a large ...
From $264 per night (USD)Expedia
- Click For Pricing
VRBO
Charming Annapolis home in Eastport, Now available Commissioning Week!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This delightful restored home is just 3 blocks away from the Eastport Bridge and 1.3 miles away from the Naval Academy ...
Click For PricingVRBO
- From $1050 per night (USD)
VRBO
Hidden Treasure on Weems Creek
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
STR00704 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1050 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Bay Ridge Beauty with Wooded Serenity and Community Water Views
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
STR00711 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $850 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Walk to everything! Downtown Historic Annapolis “Arts District”
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Built in 1920, the “Norfolk-Sheets House” at 39 Madison Place is a historic home, c.1904, located in the sought-after ne ...
From $700 per night (USD)VRBO
- Click For Pricing
VRBO
Cottage for Rent
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Cottage for Rent xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...
Click For PricingVRBO
- From $1045 per night (USD)
Expedia
Historic Annapolis With Parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Historic home with off-street parking for three cars and three blocks from the USNA. Across the Street from St. John Co ...
From $1045 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Dog-friendly house with yard, deck, firepit, washer\/dryer & AC - near golf
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Seas The Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $318 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
Beautiful colonial only 3 miles to the Naval Academy!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Beautiful colonial perfect for Naval Academy commissioning week! Bedrooms 6 - Baths: 2.5 Sleeps 11 comfortably. Finish ...
From $1200 per night (USD)Expedia
- From $529 per night (USD)
VRBO
Annapolis home, close to stadium & USNA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Walk to the Annapolis Navy-Marine Corp Stadium for games, or just a few mins by car to USNA and downtown. This delightf ...
From $529 per night (USD)VRBO
- From $841 per night (USD)
Expedia
Riverfront home with private dock, foosball table, fireplace, river views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Taids Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $841 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Historic district home, View of the Capital, WALK Downtown, w\/ Outdoor Dining!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Newly renovated w ...
From $500 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront Oasis w Boat Dock & Backyard BBQ
- Bedrooms:
- 3
- Bathrooms:
- 0
- Sleeps:
- 12
Experience the epitome of waterfront living at our exquisite 4-bedroom home, nestled just moments away from the serene M ...
Click For PricingExpedia
- From $195 per night (USD)
VRBO
Cozy Maryland Retreat Near Sandy Pointe State Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the best of Annapolis with ease from this updated 3-bedroom, 1-bathroom home! The vacation rental has all the e ...
From $195 per night (USD)VRBO
- From $366 per night (USD)
Expedia
Belle By the Bay- Great location and parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
As soon as you enter this beautiful two-floor home, you'll be greeted by the modern yet very comfortable open-concept de ...
From $366 per night (USD)Expedia
- From $558 per night (USD)
VRBO
Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W\/D
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
The Salty Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $558 per night (USD)VRBO
- Click For Pricing
Expedia
Upscaled Efficiency Apartment in Private Community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
800 sq ft of newly designed apartment with full size kitchen, full size bathroom, lots of storage space, laundry room wi ...
Click For PricingExpedia
- From $316 per night (USD)
VRBO
Quiet dog-friendly suburban home with patio, grill, yard, kitchen, & Pack-N-Play
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Admiral's Glen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $316 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to acco ...
From $500 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Eastport Cozy Charmer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our cottage home- the perfect location for your family & friends to enjoy Naval Academy events, boat shows, s ...
From $275 per night (USD)VRBO
- From $1429 per night (USD)
VRBO
Luxury Waterfront Annapolis\/ Private Beach & Dock
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Stunning Contemporary Home with private beach! House has been listed on another site receiving five st ...
From $1429 per night (USD)VRBO
- From $265 per night (USD)
VRBO
Historic Home with Parking Steps From Capital & USNA
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to this vibrant downtown Annapolis oasis—a unique purple parallelogram with a parking spot. From the front door, ...
From $265 per night (USD)VRBO
- From $1875 per night (USD)
VRBO
Gather together! Private wooded lot, 2 kitchens, large deck, 3 mi to downtown!
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 18
We offer you a comfortable place to gather with others and enjoy all that Annapolis has to offer. We are typically booke ...
From $1875 per night (USD)VRBO
- From $393 per night (USD)
VRBO
Go Navy West Annapolis home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two-bedroom home in West Annapolis is a charming residence that boasts a spacious back yard, providing ample outdoo ...
From $393 per night (USD)VRBO
- From $281 per night (USD)
Expedia
Charming Charles Retreat- The perfect space for fun and relaxation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibr ...
From $281 per night (USD)Expedia
- From $1150 per night (USD)
VRBO
Walk Everywhere! Your Ultimate Annapolis Retreat on Horn Point
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to your ideal rental property at 125 Chester Avenue, located in the desirable neighborhood of Horn Point in Annap ...
From $1150 per night (USD)VRBO
- From $1786 per night (USD)
Expedia
Beautiful 6 BR home on quiet, secluded lot, overlooking the Severn River
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
STR00749 - Heaven on the Severn � THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED ...
From $1786 per night (USD)Expedia
- From $328 per night (USD)
VRBO
Captain's Quarters - Eastport!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Ditch the car, bring the family & dog and make this beloved and restored 1920's bungalow in the desirable maritime commu ...
From $328 per night (USD)VRBO
- From $564 per night (USD)
Expedia
Nautical-themed home with four bedrooms, bright interior, deck, W\/D, and AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The Robins Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $564 per night (USD)Expedia
- Click For Pricing
VRBO
4 Bed & 3 Bath Contemporary in Heart of Eastport!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
DT Annapolis/ Eastport Contemporary home w open floor plan! Kitchen w large breakfast bar, SS appliances, white cabinetr ...
Click For PricingVRBO
- Click For Pricing
Expedia
Contemporary in Heart of Eastport w 2 car garage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Contemporary home with open floor plan & 2 car detached garage! Kitchen w large breakfast bar, SS appliances, white cabi ...
Click For PricingExpedia
- Click For Pricing
VRBO
2003 Craftsman; Heart of Eastport!
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Eastport Craftsman (2003). Short stroll to DT Historic Annapolis shops & Restaurants! Open floor plan! Stunning 2,464 sq ...
Click For PricingVRBO
- Click For Pricing
Expedia
Heart of Eastport 4 bedroom Modern Craftsman!
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Stunning 3,600 sq ft 4 bed/ 3 1/2 bath Contemporary Eastport Craftsman (2003). Short scenic stroll to DT Historic Annapo ...
Click For PricingExpedia
- Click For Pricing
VRBO
Mulberry's Gem
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is your home away from home. All the comforts you could need. The open concept living space is the perfect spot to ...
Click For PricingVRBO
- From $334 per night (USD)
Expedia
Remodeled 3b House-Downtown Annapolis-Private Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to this Annapolis gem located in the historic city of Annapolis. Enjoy living walking distance from all of the b ...
From $334 per night (USD)Expedia
- From $681 per night (USD)
VRBO
Two-story retreat near the harbor with a washer\/dryer, patio, & gas fireplace
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Eastport Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $681 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Cozy Arnold House Near Annapolis\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We offer a 10% military discount! Your family will be close to everything Annapolis has to offer when you stay at our co ...
From $275 per night (USD)Expedia
- From $233 per night (USD)
VRBO
Restful and Charming Home in Eastport\n
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We offer a 10% military discount upon request! A cozy home away from home in Eastport located within 1.5 Miles of Histor ...
From $233 per night (USD)VRBO
- From $441 per night (USD)
Expedia
Annapolis Family Haven
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a fantastic place for your family to stay while exploring all that Annapolis has to offer! Nestled in the quiet ...
From $441 per night (USD)Expedia
- From $421 per night (USD)
VRBO
The Crabby Patty- Your Downtown Annapolis getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibr ...
From $421 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Charming 2 BR Rancher w\/ parking and EV charger! Main floor living and just steps to the stadium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NBS23-145253 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $575 per night (USD)Expedia
- From $964 per night (USD)
VRBO
The View | Elegant house in Annapolis overlooking the river and Naval Academy
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
The View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $964 per night (USD)VRBO
- From $818 per night (USD)
Expedia
Beautiful Victorian in Great Eastport Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Available for Annapolis Boat Shows. Large historic Victorian in desirable Eastport, close to restaurants and short walk ...
From $818 per night (USD)Expedia
- From $357 per night (USD)
VRBO
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This well-appointed recently-renovated home in the heart of Annapolis is located just steps from both the Capitol and Ci ...
From $357 per night (USD)VRBO
- From $607 per night (USD)
Expedia
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $607 per night (USD)Expedia
- From $685 per night (USD)
VRBO
Wake up in luxury, walk to restaurants and stadium from West Annapolis home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this luxury craftsman-style home in West Annapolis, one block from many popular local restaurants including, ...
From $685 per night (USD)VRBO
- Click For Pricing
Expedia
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1\/2 bathrooms.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy cottage in a serene setting. A week spent in this cottage will decompress, reset, and rejuvenate. 100 year old Cott ...
Click For PricingExpedia
- From $338 per night (USD)
VRBO
Cozy suite Located in Presidents Hill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Corner House – Quaint and Cozy 2 Bedroom Suite with Parking The Corner House is a hidden gem located in the quaint P ...
From $338 per night (USD)VRBO
- From $378 per night (USD)
Expedia
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $378 per night (USD)Expedia
- From $560 per night (USD)
VRBO
Private Waterfront Woods | Dock, Kayaks, Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 19
Welcome to The Compass Rose, a serene haven with backyard shoreline surrounded by 4+ acres of pristine woods. Enjoy excl ...
From $560 per night (USD)VRBO
- From $1093 per night (USD)
Expedia
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $1093 per night (USD)Expedia
- From $483 per night (USD)
VRBO
Home with EV charger and garage parking!!Downtown Fleet Street Carriage House.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Friends! We are a USNA family (‘92) that loves this town! Walk to bottom of our street and you are at the docks. Walk to ...
From $483 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Home 2 Stay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This 2 bedroom condo has lots of extra space for your Annapolis stay. Fully stocked galley kitchen, master suite, washer ...
From $215 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Gorgeous dog-friendly retreat w\/ fireplace, patio, & firepit - centrally located
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Anchors Away Abode Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $458 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Charming Family Home in Blackwalnut Cove!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A beautiful family home located in the heart of Annapolis. Our property has a large yard for hosting and communal areas ...
From $500 per night (USD)VRBO
- From $260 per night (USD)
VRBO
Annapolis Retreat - 7 mins from downtown Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to this charming five-bedroom, two-bathroom escape in Annapolis. Located in the Hillsmere Shores neighborhood, t ...
From $260 per night (USD)VRBO
- From $483 per night (USD)
VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $483 per night (USD)VRBO
- From $521 per night (USD)
VRBO
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This home was newly renovated in 2021 and is located in the highly desirable Murray Hill Neighborhood. Conveniently loc ...
From $521 per night (USD)VRBO
- From $305 per night (USD)
VRBO
Annapolis Escape, Steps to Harbor backs to Gate 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This ground floor, private entrance condo has been fully renovated w/ new paint, floors, bath & kitchen. Queen Bed & sle ...
From $305 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Charming Eastport CapeCod
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful Cape Code made for entertaining, this Eastport home is perfect for your next trip to Annapolis! Newly renovate ...
From $475 per night (USD)VRBO
- From $483 per night (USD)
VRBO
Hillbottom Hideaway Beachhouse - Severna Park pet friendly! With hot tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience living by the water in our beautifully renovated 3-bedroom, 2-bathroom three level home. With stunning water ...
From $483 per night (USD)VRBO