South River, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in South River, Maryland on RentalSaver.com!

South River Rentals

From $518 per night (USD)
VRBO
Great Entertaining Spot for any Occassion!
Bedrooms:
1
Bathrooms:
2
Sleeps:
10
This newly built 2012 Carriage House has all the bells and whistles for a relaxed fiiends and family stay. Enjoy this u ...
From $518 per night (USD)
VRBO
From $239 per night (USD)
VRBO
New Bungalow with view of South River!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern bungalow that ha ...
From $239 per night (USD)
VRBO
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VRBO
Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nice 2 bedrooms / 1 bathroom appartment in the lower level of a single home, private entrance and patio in the back of t ...
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VRBO
From $1067 per night (USD)
Expedia
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lovely 3 bedroom house, beautifully furnished, 2 gourmet kitchens, outdoor oasis with pool, jacuzzi, sauna, steam room ...
From $1067 per night (USD)
Expedia
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VRBO
Downtown Annapolis Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two bedroom and two bathroom in Historic Annapolis, only 1 mile from arts district (west street), 2 miles from downtown ...
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VRBO
From $428 per night (USD)
Expedia
Adorable waterside cottage with pool Beach community
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
1920's two level cottage with multiple decks and a private inground swimming pool. This home boasts water views from eve ...
From $428 per night (USD)
Expedia
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VRBO
Waterfront
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Waterfront house on a point where the South River meets Boyd’s Point. House was built in 2021 with huge gourmet kitchen ...
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VRBO
From $381 per night (USD)
Expedia
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
The Beachwood Cottage is located near Mayo, Maryland, on the western shore of the Chesapeake Bay. The property sits on R ...
From $381 per night (USD)
Expedia
From $319 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 $319 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 $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 $337 per night (USD)
Expedia
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Treat yourself to the best while in Annapolis! Gorgeous 1500 sq. ft. custom designed waterfront apartment that takes fu ...
From $337 per night (USD)
Expedia
From $303 per night (USD)
VRBO
The Yellow Cottage on Harness Creek
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The minute you step into our charming waterfront cottage you will feel right at home! Situated on Harness Creek, in a q ...
From $303 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Mins to Annapolis from Waterfront Retreat w Stunning Views of the 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 $567 per night (USD)
Expedia
From $1670 per night (USD)
VRBO
Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Newly Renovated with larger bedrooms and 2 more bathrooms! Enjoy Annapolis with family & friends all year at this extrao ...
From $1670 per night (USD)
VRBO
From $582 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 $582 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Charming Annapolis Guest House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming guest house with private access is in a great location! Just 2 miles from the Naval Academy, Downtown Anna ...
From $327 per night (USD)
VRBO
From $186 per night (USD)
Expedia
New Loft w/South River view from treehouse deck!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that h ...
From $186 per night (USD)
Expedia
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 $1563 per night (USD)
VRBO
Commissioning Week Escape with Pool and Beautiful 4 Seasons room
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
STR00808 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1563 per night (USD)
VRBO
From $1269 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 $1269 per night (USD)
VRBO
From $940 per night (USD)
Expedia
Clean, Spacious Family House
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
5 bedrooms (sleeps 9). First-floor wheelchair accessible bedroom with ADA compliant bathroom. Entertaining kitchen and p ...
From $940 per night (USD)
Expedia
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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VRBO
Vacation house near Downtown Annapolis
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Enjoy a weekend away in a secluded house in a lovely neighborhood right outside Annapolis. Our house is set back from th ...
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VRBO
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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 ...
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Expedia
From $193 per night (USD)
VRBO
A Serene Tiny Home Experience
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnish ...
From $193 per night (USD)
VRBO
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Expedia
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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Expedia
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
From $588 per night (USD)
Expedia
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to La Maison, a light-filled, stylish 4-bedroom, 2.5-bath waterfront retreat on the South River—just minutes fro ...
From $588 per night (USD)
Expedia
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VRBO
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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VRBO
From $315 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 $315 per night (USD)
VRBO
From $778 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 $778 per night (USD)
VRBO
From $826 per night (USD)
Expedia
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 $826 per night (USD)
Expedia
From $1833 per night (USD)
VRBO
Riverfront Retreat 7mil from MD Renaissance Fest!
Bedrooms:
7
Bathrooms:
10
Sleeps:
28
Welcome to your serene retreat on the South River! The heart of this expansive estate is a charming cottage with 5 bedro ...
From $1833 per night (USD)
VRBO
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Expedia
Luxe Waterside Escape with Pool & Hot Tub
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to The Luxe! A newly renovated 5 bedroom 3.5 bath home on the South River, 15 minutes outside of Annapolis & Nav ...
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Expedia
From $419 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 $419 per night (USD)
VRBO
From $1662 per night (USD)
Expedia
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 $1662 per night (USD)
Expedia
From $1042 per night (USD)
VRBO
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 $1042 per night (USD)
VRBO
From $609 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 $609 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from ...
From $521 per night (USD)
VRBO
From $773 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 $773 per night (USD)
Expedia
From $418 per night (USD)
VRBO
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)
VRBO
From $1121 per night (USD)
Expedia
Serene Sunsets at Historic Waterfront 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 $1121 per night (USD)
Expedia
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Expedia
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 ...
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Expedia
From $522 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 $522 per night (USD)
Expedia
From $284 per night (USD)
VRBO
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Song of River City Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $284 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $527 per night (USD)
VRBO
Bay Poolhouse
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Bay Pool House License number 000268 ...
From $527 per night (USD)
VRBO
From $485 per night (USD)
VRBO
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
The charming home is a 3 bedroom 2 full bath that's been professionally decorated and has exotic tiger hardwood flooring ...
From $485 per night (USD)
VRBO
From $525 per night (USD)
VRBO
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)
VRBO
From $2009 per night (USD)
VRBO
Spacious 6-Bedroom Waterfront Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
WATERFRONT — Available commissioning week 2026, booked commissioning 2027. Beautiful Nantucket style home right on the S ...
From $2009 per night (USD)
VRBO
From $196 per night (USD)
VRBO
Cozy Home in Beautiful Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Keep it simple at this peaceful and centrally located Annapolis home. It has all the amenities and essentials of a home ...
From $196 per night (USD)
VRBO
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Expedia
Old home with Million dollar view
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Old home with million dollar view. New bed & bedding. So many good restaurants nearby. Waterfront with deck & dock. Down ...
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Expedia
From $540 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 $540 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Searenity Stays, a Cozy Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Furnished, Cozy Home (3 Bd, 2 Bth) Near Chesapeake Bay, Parks & Playgrounds Relax and enjoy your time with family and fr ...
From $289 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Bring your boat, your fishing gear, and your appetite for coastal charm! This 3BR/2BA Annapolis cottage offers access to ...
From $532 per night (USD)
VRBO
From $1261 per night (USD)
VRBO
Waterfront Architectural Masterpiece with private dockage available.
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Heron Point House is an owner imagined home, designed by one of the region's leading architects and built to perfection. ...
From $1261 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $141 per night (USD)
VRBO
From $1929 per night (USD)
Expedia
On the Waterfront Custom Chalet w Multiple Suites, Private Pier and Hot Tub in Edgewater
Bedrooms:
6
Bathrooms:
6
Sleeps:
15
Escape to this spectacular custom-built waterfront estate in Edgewater, MD—just 15 minutes from downtown Annapolis. Styl ...
From $1929 per night (USD)
Expedia
From $424 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 $424 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Belle By The Bay Summ
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Summary: This lovely home has 3 bedrooms, 2.5 bathrooms, fully equipped kitchen with large island that seats 4 and an ou ...
From $340 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
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Expedia
Lakefront House- near downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Great place to relax and enjoy the serene view of the lake in this spacious house with multiple balconies. Enjoy a hotel ...
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Expedia
From $735 per night (USD)
VRBO
Get Ready for Blissful Getaway! Short Drive to Chase Lloyd House, Pet-Friendly
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $735 per night (USD)
VRBO
From $490 per night (USD)
VRBO
Spacious Good-Value Accommodation! w/ Outdoor Pool, Pet-Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $490 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Enjoy a Hassle-Free Stay! Pet-Friendly, Close to William Paca Garden
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $250 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Beach cottage with firepit, grill, outdoor areas, AC, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Pine Whiff Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $610 per night (USD)
Expedia
From $388 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 & Garden ...
From $388 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Edgewater/Mayo Gateaway w/ Hot Tub
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 $493 per night (USD)
Expedia
From $283 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 $283 per night (USD)
VRBO
From $1318 per night (USD)
Expedia
The Fritz! - South River Waterfront with Elevator
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Summary: Resting on the peaceful shores of the South River, "The Fritz" is a timeless, elegant waterfront retreat, cher ...
From $1318 per night (USD)
Expedia
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 $538 per night (USD)
Expedia
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)
Expedia
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 $1181 per night (USD)
Expedia
Six bedroom 2020 Fountaine Pajot catamaran
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Beautiful 6 bedroom 6 bathroom catamaran just miles from downtown Annapolis on the South River from June to November. Sa ...
From $1181 per night (USD)
Expedia
From $3100 per night (USD)
VRBO
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Why rent a hotel when you can be in a Floatel on a Fountaine Pajot Saba luxurious 50 foot catamaran six Cabin six head l ...
From $3100 per night (USD)
VRBO
From $535 per night (USD)
Expedia
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Anchors Away Abode Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $535 per night (USD)
Expedia
From $573 per night (USD)
VRBO
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)
VRBO
From $570 per night (USD)
Expedia
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)
Expedia
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VRBO
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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VRBO
From $299 per night (USD)
Expedia
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)
Expedia
From $293 per night (USD)
VRBO
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)
VRBO
From $383 per night (USD)
Expedia
Riverview Retreat on Warehouse Creek - sleeps 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Riverview Retreat on Warehouse Creek is a renovated, cozy, and luxurious guest house, offering families and gr ...
From $383 per night (USD)
Expedia
From $697 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 $697 per night (USD)
VRBO
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Expedia
Dock, Dine, & Unwind: The Ultimate Waterfront Glamp Spot
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 ...
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Expedia
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VRBO
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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VRBO
From $209 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 $209 per night (USD)
VRBO
From $179 per night (USD)
VRBO
Water view studio. 20 minutes from Annapolis.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This property is an efficiency that sits on top of a garage in a quiet neighborhood. The perfect place to stay while ta ...
From $179 per night (USD)
VRBO
From $149 per night (USD)
VRBO
Minutes from History: Room w/ Free Breakfast Near Downtown Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $149 per night (USD)
VRBO
From $167 per night (USD)
VRBO
Our Welcoming Suite in Annapolis Near Historic Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $167 per night (USD)
VRBO
From $151 per night (USD)
VRBO
Annapolis Adventure: Room w/ Outdoor Pool + Easy Access to Historic Sites
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $151 per night (USD)
VRBO
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VRBO
Grandma’s Summer House @ Beverly Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Grandma's Summer House @ Beverly Beach, our newly renovated getaway! Whether you're planning a shor ...
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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 $157 per night (USD)
VRBO
Experience Historical Annapolis + Complimentary Breakfast! Outdoor Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $157 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Holly Hill Haven - Sleeps 10
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Escape to our beautifully renovated home in the heart of the scenic Mayo Peninsula! Nestled in the charming co ...
From $461 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Wright's Cottage- Pet's Welcome & EV Charging
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, larg ...
From $184 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
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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 ...
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VRBO
From $617 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 $617 per night (USD)
Expedia

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