South River Rentals
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Indoor Soft Hot Tub - Family Stay @ The Cape!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make some memories at this unique and family-friendly place. Family Friendly Staycation fully outfitted to accommodate ...
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From $443 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 $443 per night (USD)Expedia
From $445 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 $445 per night (USD)VRBO
From $953 per night (USD)Expedia
Captain's Retreat! Newly Renovated - few steps from the beach!
- Bedrooms:
- 3
- 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 $614 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 $614 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 $506 per night (USD)VRBO
Gorgeous dog-friendly retreat w\/ fireplace, patio, & firepit
- 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 $506 per night (USD)VRBO
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Downtown Annapolis Luxury House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our downtown luxury cottage is located 1.4 miles from Church Circle, which is the heart of downtown Annapolis. We are wa ...
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From $258 per night (USD)VRBO
Sailboat Experience in Annapolis
- Bedrooms:
- 2
- 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 $258 per night (USD)VRBO
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Amazing townhome in Annapolis, near Restaurants, USNA, Shopping centers, & more
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 3
Amazing three bedroom townhome with Masters suite(with full bathroom), and 2 additional bedrooms with access to one full ...
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From $357 per night (USD)VRBO
Riverview Retreat on Warehouse Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Riverview Retreat on Warehouse Creek is a renovated, cozy, and luxurious guest house, offering families and groups a ser ...
From $357 per night (USD)VRBO
From $678 per night (USD)VRBO
Waterfront Getaway - Dock UR Boat & Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Luxurious Waterfront Escape in Annapolis ◉ Private Beach Access: Step right onto the shore for a peaceful retreat ◉ Arch ...
From $678 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 $514 per night (USD)Expedia
Mins to Downtown in Waterfront community at Pet-friendly Pinecrest Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Just minutes from Downtown Annapolis, this charming Cape is located in a quiet water-privileged neighborhood with easy a ...
From $514 per night (USD)Expedia
From $1535 per night (USD)VRBO
Splendid home w\/private pool, fire pit, several decks & balconies
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Porter Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1535 per night (USD)VRBO
From $568 per night (USD)Expedia
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Water-lovers dream waterfront cottage 15 min to Annapolis, Navy Academy & 40 min from DC with perfect paddleboarding wat ...
From $568 per night (USD)Expedia
From $480 per night (USD)VRBO
Spacious home with bay views, deck, balcony and gas grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Oyster Harbor Waterview Home Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $480 per night (USD)VRBO
From $314 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 $314 per night (USD)Expedia
From $237 per night (USD)VRBO
Home 2 Stay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 2 bedroom condo has lots of extra space for your Annapolis stay. Fully stocked galley kitchen, master suite, washer ...
From $237 per night (USD)VRBO
From $733 per night (USD)VRBO
This tent is a 0 bedroom(s), 1 bathrooms, located in Edgewater, MD.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 16
Escape it all this winter with a cozy retreat under the stars—set up camp for an intimate waterfront glamping experience ...
From $733 per night (USD)VRBO
From $860 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 $860 per night (USD)VRBO
From $329 per night (USD)VRBO
Charming 3BDR Bungalow Near Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Stay in a clean, comfortable bungalow near scenic Annapolis! With 3 bedrooms, 2 baths, ample parking, and a fully stock ...
From $329 per night (USD)VRBO
From $1725 per night (USD)VRBO
Waterfront Escape Near Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 26
A perfect getaway in a quiet neighborhood with access to Whitemarsh Creek, Rhode River & Chesapeake Bay. Beautiful horse ...
From $1725 per night (USD)VRBO
From $565 per night (USD)Expedia
Available for CW 2025 Waterfront neighborhood, with fenced-in yard and dog-friendly
- Bedrooms:
- 3
- 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 $565 per night (USD)Expedia
From $394 per night (USD)VRBO
London Towne Bungalow w\/Loft - Walk to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This charming London Towne Bungalow is just a short walk from Edgewater Park and Historic London Town & Gardens, a histo ...
From $394 per night (USD)VRBO
From $544 per night (USD)Expedia
Edgewater\/Mayo Getaway!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming, spacious single-family home in the heart of Mayo, perfect for families or groups. Comfortably sleeps 6 with sp ...
From $544 per night (USD)Expedia
From $396 per night (USD)VRBO
Waterfront Getaway, Dock Your Boat & Play!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Dock your boat or park your car and enjoy an expansive waterfront escape! Our brand-new guest unit offers all the amenit ...
From $396 per night (USD)VRBO
From $947 per night (USD)Expedia
Serene waterfront sunsets in this sprawling historic Annapolis home
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 10
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sit ...
From $947 per night (USD)Expedia
From $575 per night (USD)VRBO
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Available for Commissioning Week 2025! Located in the Annapolis "Republic of Eastport", this charming pet-friendly home ...
From $575 per night (USD)VRBO
From $540 per night (USD)Expedia
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 $540 per night (USD)Expedia