South River Rentals
From $1630 per night (USD)VRBO
Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 14
(20% Off 7/7-7/18) Newly Renovated with larger bedrooms and 2 more bathrooms! Enjoy Annapolis with family & friends all ...
From $1630 per night (USD)VRBO
From $350 per night (USD)Expedia
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 $350 per night (USD)Expedia
From $372 per night (USD)VRBO
Coastal Edgewater Home w/ Private Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Your next maritime retreat awaits at this 5-bedroom, 2-bath Edgewater vacation rental! Featuring 2 Smart TVs, a fully eq ...
From $372 per night (USD)VRBO
From $953 per night (USD)Expedia
Captain's Retreat! Newly Renovated - few steps from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay! Steps to the Beach and ...
From $953 per night (USD)Expedia
From $509 per night (USD)VRBO
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Water-lovers dream waterfront cottage 15 min to Annapolis, Navy Academy & 40 min from DC with perfect paddleboarding wat ...
From $509 per night (USD)VRBO
From $677 per night (USD)Expedia
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 $677 per night (USD)Expedia
From $705 per night (USD)VRBO
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)VRBO
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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 $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 $918 per night (USD)Expedia
Splendid home w/private pool, fire pit, several decks & balconies
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Porter Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $918 per night (USD)Expedia
From $460 per night (USD)VRBO
Riverview Retreat on Warehouse Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Riverview Retreat on Warehouse Creek is a cozy, renovated basement apartment guest house attached to a private ...
From $460 per night (USD)VRBO
From $763 per night (USD)VRBO
Annapolis Waterfront: Dock ur Boat & Walk 2 Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
◉ 5-min stroll to private beach ◉ Dock access for your boat ◉ Gourmet kitchen + private chef (by request) ◉ Stunning ...
From $763 per night (USD)VRBO
From $239 per night (USD)VRBO
Sailboat Experience in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Choosingthis C and C 33 sailboat for your stay is opting for an experience over extravagance. It's about immersing yours ...
From $239 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
From $798 per night (USD)VRBO
Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This clean, peaceful, 5 BR, 4 BA house features a waterfront view from 2 spacious decks in a quiet community. Perfect fo ...
From $798 per night (USD)VRBO
From $316 per night (USD)VRBO
Charming 3BDR Bungalow Near Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in a clean, comfortable bungalow near scenic Annapolis! With 3 bedrooms, 2 baths, ample parking, and a fully stock ...
From $316 per night (USD)VRBO
From $2048 per night (USD)VRBO
Waterfront Escape Near Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 26
A perfect getaway in a quiet neighborhood with access to Whitemarsh Creek, Rhode River & Chesapeake Bay. Beautiful horse ...
From $2048 per night (USD)VRBO
From $426 per night (USD)Expedia
Waterfront Family-Friendly Community, Fenced-In Yard and Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Still available for Commissioning Week 2025! Welcome to the Shore Leave! Just a five minute walk to the beach, five mi ...
From $426 per night (USD)Expedia
From $488 per night (USD)VRBO
London Towne Bungalow w/Loft - Walk to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This charming London Towne Bungalow is just a short walk from Edgewater Park and Historic London Town & Gardens ...
From $488 per night (USD)VRBO
From $541 per night (USD)Expedia
Edgewater/Mayo Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Charming, spacious single-family home in the heart of Mayo, perfect for families or groups. Comfortably sleeps ...
From $541 per night (USD)Expedia
From $344 per night (USD)VRBO
Waterfront Getaway, Dock Your Boat & Play!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: Dock your boat or park your car and enjoy an expansive waterfront escape! Our brand-new guest unit offers all ...
From $344 per night (USD)VRBO
From $308 per night (USD)Expedia
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 $308 per night (USD)Expedia
From $1140 per night (USD)VRBO
Serene Waterfront Sunsets from Sprawling Historic Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sit ...
From $1140 per night (USD)VRBO
From $530 per night (USD)Expedia
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Available for Commissioning Week 2025! Located in the Annapolis "Republic of Eastport", this charming pet-friendly home ...
From $530 per night (USD)Expedia
From $545 per night (USD)VRBO
7 mins away from Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
Come stay at our cozy house. Perfect for a group of 11people. Share beautiful memories that will last a lifetime. Close ...
From $545 per night (USD)VRBO