Peninsula Park Rentals
- From $1367 per night (USD)
VRBO
Indoor\/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
STR21-144966 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1367 per night (USD)VRBO
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Expedia
Private Pet-friendly Coastal Suite with water views just minutes to Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Be sure to ask about renting the entire home for Commissioning Week and special Annapolis events. Enjoy the serene wa ...
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VRBO
Annapolis Family Vacation Rental: Close to downtown and the Naval Academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Located: 4.1mi (10 min) from Naval Academy: Annapolis Cove Neighborhood Open floor plan: Kitchen open to living room/sc ...
Click For PricingVRBO
- From $1164 per night (USD)
Expedia
Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1164 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Lovely contemporary in water-privileged community
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Well-furnished contemporary home, great for families, located in a quiet family-friendly neighborhood. This home has 3 ...
From $450 per night (USD)VRBO
- From $643 per night (USD)
VRBO
DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added out ...
From $643 per night (USD)VRBO
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VRBO
Look How Close! Annapolis gem near City Dock, USNA, Walk to Main & Market!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
ABOUT THE LOCATION: Just 1/4 mile walk to: — top restaurants (incl. Main & Market, Jack’s Fortune, and Starbucks) — publ ...
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Expedia
Cute, cozy rancher close to down town Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private location with plenty of parking. Newly renovated bathroom, french doors open to deck; great for indoor-outdoor l ...
Click For PricingExpedia
- From $420 per night (USD)
VRBO
Quiet Home Close to Downtown Annapolis and Parks
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This private single family home is located on a quarter acre and is just minutes to everything Annapolis has to ...
From $420 per night (USD)VRBO
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Expedia
Annapolis House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
Click For PricingExpedia
- From $296 per night (USD)
VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $296 per night (USD)VRBO
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Expedia
Easy Annapolis lodging - still available for Sailboat Show!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This home (divided/upper floor only) is perfect for families, situated on a quiet residential street with a gorgeous bac ...
Click For PricingExpedia
- From $714 per night (USD)
VRBO
Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Base Camp on the Lake Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $714 per night (USD)VRBO
- From $1020 per night (USD)
Expedia
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The Morning Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1020 per night (USD)Expedia
- From $1585 per night (USD)
VRBO
Lakefront home with private pool, hot tub, outdoor space, central AC, & W\/D
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1585 per night (USD)VRBO
- From $397 per night (USD)
Expedia
Jackson's Bunker in Eastport with fenced-in backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the Annapolis "Republic of Eastport", this charming pet-friendly home is a short walk to restaurants, shops, ...
From $397 per night (USD)Expedia
- From $402 per night (USD)
VRBO
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...
From $402 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Quiet Neighborhood 2.3 miles from Downtown w\/FREE parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Spinnakers Run, nestled just 2.3 miles from Historic Downtown Annapolis and Eastport with plenty of free park ...
From $375 per night (USD)VRBO
- From $164 per night (USD)
VRBO
Indulge or be still near Naval Academy\/ Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Beautifully decorated apt. close to the Naval Academy /historic downtown Annapolis. East port too. Waterview. Amazing su ...
From $164 per night (USD)VRBO
- From $120 per night (USD)
VRBO
My Annapolis Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FOUR WEEK MINIMUM STAY beginning July 1st. This fully furnished studio apartment has everything you'll need for a quiet ...
From $120 per night (USD)VRBO
- From $809 per night (USD)
VRBO
Annapolis Villa Aquamarine
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Annapolis and its very own Villa Aquamarine: your exclusive oasis awaits in this exceptional five bedroom hom ...
From $809 per night (USD)VRBO
- From $1121 per night (USD)
Expedia
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Annapolis Bay Ridge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $1121 per night (USD)Expedia
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VRBO
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 PricingVRBO
- From $1436 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 $1436 per night (USD)VRBO
- From $251 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 $251 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to my home! This open concept 3 bedroom (all queens) 1.5 bath cottage has a large, fenced yard and backs up to ...
From $263 per night (USD)VRBO
- From $507 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 $507 per night (USD)VRBO
- From $175 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 $175 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 $295 per night (USD)
Expedia
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 $295 per night (USD)Expedia
- From $395 per night (USD)
VRBO
Annapolis House Minutes from Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This Quiet peaceful location with Spacious 4 bedroom, 2 full and 1 half bath is just 3 miles from Downtown Annapolis. Pe ...
From $395 per night (USD)VRBO
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Expedia
Annapolis Charmer! 2BR Bright BSMT APT 3 mi to DT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Quiet, cozy established single family neighborhood with a huge yard. Take in the history/music scene a ...
Click For PricingExpedia
- From $272 per night (USD)
VRBO
Bay Ridge house by Quiet Waters Park, Thomas Point Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All f ...
From $272 per night (USD)VRBO
- From $233 per night (USD)
Expedia
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Property is 2 bedrooms and 1 bathroom furnished with brand new furniture. Bedrooms have fitted with comfortable queen si ...
From $233 per night (USD)Expedia
- From $1325 per night (USD)
VRBO
Sailor's Caribbean FantaSea -5 BR Creekside Contemporary with Private Dock and Water Taxi Service
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
STR23-145260 - THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM MEM ...
From $1325 per night (USD)VRBO
- From $1808 per night (USD)
Expedia
Newly Updated EV Charger Ready Peaceful Home in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our stylish and modern home, where comfort meets convenience! Here's what you can expect during your stay: ✔ ...
From $1808 per night (USD)Expedia
- From $471 per night (USD)
VRBO
Ahoy! The Buccaneer awaits you just outside Annapolis - fenced-in yard and rec room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. Thi ...
From $471 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Annapolis Home on Black Walnut Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Single Family home on Black Walnut Creek located in the Bay Highlands community, Annapolis, MD https://www.bayhighlands. ...
From $375 per night (USD)Expedia