Peninsula Park Rentals
From $1522 per night (USD)VRBO
Indoor/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Waterfront Luxury Retreat in Eastport with Year-Round Indoor Pool, Private Dock, & Kayaks Description Your indoor and o ...
From $1522 per night (USD)VRBO
From $321 per night (USD)VRBO
Lovely contemporary in water-privileged community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Well-furnished contemporary home, great for families, located in a quiet family-friendly neighborhood. This home has 3 ...
From $321 per night (USD)VRBO
From $733 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 $733 per night (USD)VRBO
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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 ...
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From $349 per night (USD)VRBO
Quiet Home Close to Downtown Annapolis and Parks
- Bedrooms:
- 3
- 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 $349 per night (USD)VRBO
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Annapolis House
- Bedrooms:
- 3
- 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 ...
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From $382 per night (USD)VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $382 per night (USD)VRBO
From $418 per night (USD)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 ...
From $418 per night (USD)Expedia
From $3784 per night (USD)VRBO
Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
- Bedrooms:
- 4
- 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 $3784 per night (USD)VRBO
From $1774 per night (USD)Expedia
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The Morning Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1774 per night (USD)Expedia
From $1626 per night (USD)VRBO
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
- Bedrooms:
- 4
- 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 $1626 per night (USD)VRBO
From $525 per night (USD)Expedia
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
- 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 $525 per night (USD)Expedia
From $490 per night (USD)VRBO
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
- Bedrooms:
- 3
- 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 $490 per night (USD)VRBO
From $1326 per night (USD)Expedia
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Annapolis Bay Ridge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $1326 per night (USD)Expedia
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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 ...
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From $1243 per night (USD)VRBO
Luxury Waterfront Annapolis home with your very own Private Beach & Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Stunning Contemporary Home with private beach! House has been listed on another site receiving five st ...
From $1243 per night (USD)VRBO
From $393 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 $393 per night (USD)VRBO
From $357 per night (USD)VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to my home! I hope that you love it as much as I do. It is an open concept 3 bedroom (two queens and a king) 1 ...
From $357 per night (USD)VRBO
From $635 per night (USD)VRBO
Private Waterfront Woods | Dock, Kayaks, Views
- Bedrooms:
- 3
- 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 $635 per night (USD)VRBO
From $573 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 nestled in the Hillsmere Shores neighborhood of Annapolis. Ju ...
From $573 per night (USD)Expedia
From $570 per night (USD)VRBO
Annapolis House Minutes from Downtown
- Bedrooms:
- 2
- 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 $570 per night (USD)VRBO
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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 ...
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From $299 per night (USD)VRBO
Bay Ridge house by Quiet Waters Park, Thomas Point Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All f ...
From $299 per night (USD)VRBO
From $293 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 $293 per night (USD)Expedia
From $1338 per night (USD)VRBO
Fabulous Waterfront Contemporary with Rooftop Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
RENT-000856-2025 THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM M ...
From $1338 per night (USD)VRBO
From $284 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 $284 per night (USD)Expedia
From $550 per night (USD)VRBO
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
- 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 $550 per night (USD)VRBO
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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 ...
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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 $1413 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 $1413 per night (USD)VRBO
From $604 per night (USD)VRBO
Annapolis Home Near Beach & Quiet Waters Park!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Discover your next peaceful escape in our charming retreat! Nestled in a warm, inviting space, this cozy home offers bri ...
From $604 per night (USD)VRBO
From $585 per night (USD)VRBO
Pet-Friendly & Spacious Home in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Spacious 4BR/2.5BA home roughly 10 mins from Downtown Annapolis - close to the action, yet tucked in a quiet ne ...
From $585 per night (USD)VRBO
From $685 per night (USD)VRBO
Quiet Waters Family Home 4BR Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to this charming Hillsmere Shores retreat, in one of Annapolis’ top waterfront neighborhoods. Just min ...
From $685 per night (USD)VRBO