Fishing Creek Rentals
Click For PricingVRBO
Bay Poolhouse
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Bay Pool House License number 000268 ...
Click For PricingVRBO
From $610 per night (USD)Expedia
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Beachfront w/Bay Bridge view - Wake up to a beautiful view of the sunrise over the Chesapeake Bay. Go to sleep ...
From $610 per night (USD)Expedia
Click For PricingVRBO
Studio, water community, private entrance, paver patio, off street parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Cozy studio, water access community with oversized windows facing large fenced yard with private paver patio, private en ...
Click For PricingVRBO
From $546 per night (USD)Expedia
Water Views - Close to Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city onl ...
From $546 per night (USD)Expedia
From $303 per night (USD)VRBO
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay ...
From $303 per night (USD)VRBO
From $245 per night (USD)Expedia
Private Cottage on gated estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapo ...
From $245 per night (USD)Expedia
From $550 per night (USD)VRBO
Tranquil Waterfront Retreat w Stunning Views of the Chesapeake Bay and Bridge with Fenced-In Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks! Escape to a tranquil waterfront retreat ...
From $550 per night (USD)VRBO
From $704 per night (USD)Expedia
Water-view escape with WFH desk & entertainer's deck - dog-friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Cardinal's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $704 per night (USD)Expedia
From $377 per night (USD)VRBO
Pet-Friendly Annapolis Home: Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the perfect blend of comfort and adventure at this 3-bed, 2-bath Annapolis vacation rental! Start your day wi ...
From $377 per night (USD)VRBO
From $376 per night (USD)Expedia
Cozy Cottage with Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for groups of 4 wanting to be near Annapolis and the Chesapeake Bay, but far enough away for peace, quiet, and e ...
From $376 per night (USD)Expedia
From $752 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 $752 per night (USD)VRBO
From $726 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 $726 per night (USD)VRBO
From $597 per night (USD)VRBO
Chesapeake Bay single family home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Quaint community of Arundel on the Bay in Annapolis, Maryland. Spacious 4 bedroom, 3.5 bathrooms in 3000 s.f. waterfront ...
From $597 per night (USD)VRBO
From $633 per night (USD)VRBO
Coastal Cottage - 3 BR -Retreat Near Annapolis | Bay Views | Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STR-000324 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $633 per night (USD)VRBO
From $1155 per night (USD)VRBO
Complete WATERFRONT LIVING! 5 BR in Quiet Waterfront Community
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
STR-250 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1155 per night (USD)VRBO
From $589 per night (USD)Expedia
Charming Annapolis WaterVIEW Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters o ...
From $589 per night (USD)Expedia
From $801 per night (USD)VRBO
Charming Cottage with Hot Tub 1 Block from the Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy Annapolis with family & friends all year at this fully stocked and freshly renovated cottage just a block from the ...
From $801 per night (USD)VRBO
From $1261 per night (USD)Expedia
Commissioning Week by the Bay! 2027/8 Available!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Available for CW 2027-2028 at $7,700. 5 bedroom, 3.5 bath located 5 miles from Gate 1 in the waterfront community of Aru ...
From $1261 per night (USD)Expedia
From $416 per night (USD)VRBO
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom bungalow in Annapolis is perfect for your escape. With 2 full beds and 1 full sofa bed in the 3rd room. I ...
From $416 per night (USD)VRBO
From $637 per night (USD)Expedia
Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Available for Commissioning Week 2025! Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks Welcome to the ...
From $637 per night (USD)Expedia
From $352 per night (USD)VRBO
Entire house on quiet street w/fenced yard—1 block from river, 3 from bay
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Arundel-on-the-Bay is a private community on Annapolis Neck peninsula, and this home sits right in the middle. Ideal sp ...
From $352 per night (USD)VRBO
Click For PricingExpedia
Waterfront Estate w/ Private Beach + Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Private Nantucket style waterfront estate w/ beach, deep water slips and a 180 waterview. Expansive western sunsets on F ...
Click For PricingExpedia
From $538 per night (USD)VRBO
Sunny and spacious water view/access home in Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The property is all set up for boating and fishing with a drive-thru driveway. It is located one block from the boat ram ...
From $538 per night (USD)VRBO
Click For PricingExpedia
Waterfront Beach House with amazing views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The perfect place to experience amazing sunrise/sunset views on the water, beach within walking distance, restaurants, d ...
Click For PricingExpedia
From $953 per night (USD)VRBO
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)VRBO
From $1630 per night (USD)Expedia
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)Expedia
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 $1139 per night (USD)Expedia
Spacious home with an outdoor pool, screened porch, washer/dryer & central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Thomas Point Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $1139 per night (USD)Expedia
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