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

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VRBO
Waterfront
Bedrooms:
6
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
$Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis \/USNA$
From $405 per night (USD)
Expedia
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 $405 per night (USD)
Expedia
From $3373 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 $3373 per night (USD)
VRBO
From $553 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 $553 per night (USD)
Expedia
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VRBO
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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VRBO
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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 $618 per night (USD)
VRBO
Water Views - Close to Downtown Annapolis
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city onl ...
From $618 per night (USD)
VRBO
From $353 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 $353 per night (USD)
Expedia
From $370 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 $370 per night (USD)
VRBO
From $242 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 $242 per night (USD)
Expedia
$Nice retreat apartment\/private patio, min. away from USNA & Downtown Annapolis$
From $283 per night (USD)
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 ...
From $283 per night (USD)
VRBO
$New Loft w\/South River view from treehouse deck!$
From $147 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 $147 per night (USD)
Expedia
From $224 per night (USD)
VRBO
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 $224 per night (USD)
VRBO
From $472 per night (USD)
Expedia
All on 1 level water-privileged community with private deck, screened porch and backyard
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season Escape to a tranquil waterfront retreat with stunning views of th ...
From $472 per night (USD)
Expedia
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VRBO
Vacation house near Downtown Annapolis
Bedrooms:
5
Bathrooms:
8
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 $378 per night (USD)
VRBO
Family and Pet-friendly Edgewater cottage with hot tub in waterfront community
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Visit the magic of Annapolis during the Holiday Season Welcome to this charming cottage located in a water-privileged co ...
From $378 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Adorable waterside cottage with pool Beach community
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1920's two level cottage with multiple decks and a private inground swimming pool. This home boasts water views from eve ...
From $304 per night (USD)
Expedia
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VRBO
Annapolis House
Bedrooms:
4
Bathrooms:
5
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
$Annapolis Cozy Beachfront\/Waterfront w\/Chesapeake Bay Bridge view$
From $593 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 $593 per night (USD)
Expedia
From $1181 per night (USD)
VRBO
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)
VRBO
$Minutes from History: Room w\/ Free Breakfast Near Downtown Annapolis$
From $162 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 $162 per night (USD)
VRBO
From $186 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 $186 per night (USD)
VRBO
$Annapolis Adventure: Room w\/ Outdoor Pool + Easy Access to Historic Sites$
From $166 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 $166 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Grandma's Summer House @ Beverly Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Grandma's Summer House @ Beverly Beach, our recently renovated home. Whether you're looking for a short escap ...
From $393 per night (USD)
VRBO
From $680 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 $680 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Experience Historical Annapolis + Complimentary Breakfast! Parking
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 $181 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Splendid dog friendly home within walking distance to beach & play area
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Adventure Annapolis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $452 per night (USD)
Expedia
$Annapolis Luxury: Firepit \/ Deck \/ Grill$
From $328 per night (USD)
VRBO
Annapolis Luxury: Firepit \/ Deck \/ Grill
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to our stylish new construction in the heart of Annapolis! Our home features high ceilings, contemporary decor, ...
From $328 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Pet-Friendly Annapolis Home: Walk to Beach!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Experience the perfect blend of comfort and adventure at this 3-bed, 2-bath Annapolis vacation rental! Start your day wi ...
From $321 per night (USD)
Expedia
$Minutes from History: 2 Relaxing Units w\/ Free Breakfast Near Downtown Annapolis$
From $382 per night (USD)
VRBO
Minutes from History: 2 Relaxing Units w\/ Free Breakfast Near Downtown Annapolis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $382 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $392 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Spacious 5-bedroom house with Pier, AC and WiFi in delightful Edgewater
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
The Annapolis area is just minutes away by land or by sea. This 5-bedroom home in Edgewater featur es 1 king bed, 2 qu ...
From $535 per night (USD)
VRBO
From $512 per night (USD)
Expedia
Annapolis Home Near Beach, Dtwn & Navy Football!
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Dog Friendly w/ Fee | Wood-Burning Fireplace | 4 Mi to Downtown Annapolis Nestled just 2 miles from the Chesapeake Bay, ...
From $512 per night (USD)
Expedia
From $386 per night (USD)
VRBO
6 Mi to Dtwn: Family-Friendly Home in Annapolis!
Bedrooms:
4
Bathrooms:
8
Sleeps:
12
Home Gym | Furnished Deck | Blackstone Grill | Near Shopping & Dining Enjoy a convenient and comfortable Maryland escap ...
From $386 per night (USD)
VRBO
$Cottage 1\/2 block to the bay$
From $353 per night (USD)
Expedia
Cottage 1\/2 block to the bay
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 $353 per night (USD)
Expedia
$Chesapeake Charm! Waterfront Property! Hot Tub! Grill - Beautiful 4 BR\/3.5 Bath$
From $582 per night (USD)
VRBO
Chesapeake Charm! Waterfront Property! Hot Tub! Grill - Beautiful 4 BR\/3.5 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Waterfront! Edgewater is waiting for you at this charming Nautical Nest! 500 feet of waterfront with 2 docks and a boat ...
From $582 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Private Waterfront Woods | Dock, Kayaks, Views
Bedrooms:
4
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 $464 per night (USD)
Expedia
From $627 per night (USD)
VRBO
La Maison - Stunning waterfront views with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Light-filled, modernly furnished 4-bedroom, 2.5 bathroom waterfront house on the South River, with a private pool - minu ...
From $627 per night (USD)
VRBO
From $307 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 $307 per night (USD)
VRBO
From $155 per night (USD)
VRBO
A Serene Tiny Home Experience
Bedrooms:
1
Bathrooms:
2
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 $155 per night (USD)
VRBO
From $312 per night (USD)
Expedia
The Yellow Cottage on Harness Creek
Bedrooms:
1
Bathrooms:
3
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 $312 per night (USD)
Expedia
$Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.$
From $1241 per night (USD)
VRBO
Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1241 per night (USD)
VRBO
$Charming 3 BR\/2BA home at Arundel on the Bay features a community beach, boat slips, playground.$
From $643 per night (USD)
Expedia
Charming 3 BR\/2BA home at Arundel on the Bay features a community beach, boat slips, playground.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
STR-000324 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $643 per night (USD)
Expedia
From $1350 per night (USD)
VRBO
4 BR Colonial home just outside of Annapolis - Beautiful 4 Seasons room overlooking fenced backyard with beautiful pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
STR00808 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1350 per night (USD)
VRBO
From $1293 per night (USD)
Expedia
UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all. 3 sides of direct bay waterfront.
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
STR-250 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1293 per night (USD)
Expedia
From $1899 per night (USD)
VRBO
A huge deck and screen porch on this contemporary cape in Edgewater offers great views of Beard's Creek and out onto the South River.
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
STR-395 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTE ...
From $1899 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 $562 per night (USD)
VRBO
Lovely contemporary in water-privileged community
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Well-furnished contemporary home, great for families, located in a quiet family-friendly neighborhood. This home has 3 ...
From $562 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
From $1077 per night (USD)
VRBO
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lovely 3 bedroom house, beautifully furnished, 2 gourmet kitchens, outdoor oasis with pool, jacuzzi, sauna, steam room ...
From $1077 per night (USD)
VRBO
From $513 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 $513 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
From $597 per night (USD)
VRBO
Chesapeake Bay single family home
Bedrooms:
4
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
$Waterfront Cottage by Annapolis w\/ Pool & Hot Tub$
From $555 per night (USD)
VRBO
Waterfront Cottage by Annapolis w\/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This home is minutes from Annapolis and within a 30 minute drive to Washington DC & 15 minutes from Navy Marine Corps Me ...
From $555 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 $561 per night (USD)
VRBO
Charming Annapolis WaterVIEW Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters o ...
From $561 per night (USD)
VRBO
From $1580 per night (USD)
Expedia
Riverfront Retreat 7mil from MD Renaissance Fest!
Bedrooms:
6
Bathrooms:
10
Sleeps:
16
Welcome to your serene retreat on the South River! The heart of this expansive estate is a charming cottage with 5 bedro ...
From $1580 per night (USD)
Expedia
From $830 per night (USD)
VRBO
Luxe Waterside Escape with Pool & Hot Tub
Bedrooms:
4
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 ...
From $830 per night (USD)
VRBO
From $561 per night (USD)
Expedia
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 $561 per night (USD)
Expedia
From $1934 per night (USD)
VRBO
Custom-built chalet w private pier and hot tub at On the Waterfront in Edgewater
Bedrooms:
7
Bathrooms:
6
Sleeps:
15
Visit the magic of Annapolis during the Holiday Season Stay at On The Waterfront in Edgewater, MD at this amazing custom ...
From $1934 per night (USD)
VRBO
From $251 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 $251 per night (USD)
Expedia
From $486 per night (USD)
VRBO
This house is a 3 bedroom(s), 2 bathrooms, located in Edgewater , MD.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Nestled in the picturesque Mayo Peninsula, our freshly renovated home in Holly Hill Harbor offers a perfect blend of ind ...
From $486 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Wright's Cottage House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wright’s Cottage offers 1 bedroom and bath. There is a full kitchen and one living room area. The back sun-room contains ...
From $164 per night (USD)
Expedia
$Commissioning Week by the Bay! 2026\/7 Available!$
From $1010 per night (USD)
VRBO
Commissioning Week by the Bay! 2026\/7 Available!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
2026-27 flat rate is $6,500; booked for 2024, 2025 5 bedroom, 3.5 bath located 5 miles from Gate 1 in the waterfront com ...
From $1010 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Edgewater's Shelby on the Bay House
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to this stunning 4-bedroom home, designed with spacious living and effortless entertaining in mind. Step inside ...
From $397 per night (USD)
Expedia
From $566 per night (USD)
VRBO
Pet Friendly-newly built house in peaceful beach community, located in Riva MD.
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Enjoy all that Annapolis has to offer in this stylish house located in Riva MD, just ten mins from downtown Annapolis, ...
From $566 per night (USD)
VRBO
From $478 per night (USD)
Expedia
New! Golden Anchor Retreat; Lux Living!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Just a 2-minute drive from Historic London Town & Gardens and near Londontowne Marina, this charming home combines comfo ...
From $478 per night (USD)
Expedia
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 $72 per night (USD)
Expedia
Charming townhome in awesome Edgewater, MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Located in Edgewater, this lovely townhome features 1 bedroom with a comfortable queen bed. Guests can enjoy amenities l ...
From $72 per night (USD)
Expedia
From $969 per night (USD)
VRBO
Perfect Townhouse for USNA Commissioning Week!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to the perfect townhouse for USNA Commissioning Week! As a former midshipman, I know how important it is to have ...
From $969 per night (USD)
VRBO
From $503 per night (USD)
VRBO
South River Retreat- Go Navy!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Located across the bridge from Annapolis. This home is located in a beautiful water privileged neighborhood on the South ...
From $503 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
Bedrooms:
2
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 $304 per night (USD)
VRBO
$Entire house on quiet street w\/fenced yard—1 block from river, 3 from bay$
From $352 per night (USD)
Expedia
Entire house on quiet street w\/fenced yard—1 block from river, 3 from bay
Bedrooms:
4
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)
Expedia
From $705 per night (USD)
VRBO
Oyster Harbor Waterfront Vacation Home -- Private Dock and Backyard
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Spacious and luxurious vacation home in Oyster Harbor, Annapolis. Features 4 bedrooms (7 beds), 3 full baths. A lively o ...
From $705 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Comfortable Townhouse Minutes from City Dock and US Naval Academy!
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Make this well-appointed townhouse your home away from home in the family-friendly Hunt Meadow community conveniently lo ...
From $342 per night (USD)
VRBO
From $1261 per night (USD)
VRBO
Waterfront Architectural Masterpiece with private dockage available.
Bedrooms:
5
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 $162 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 $162 per night (USD)
VRBO
From $1054 per night (USD)
VRBO
Spacious Contemporary Waterfront home on Chesapeake Bay's South River
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
This contemporary waterfront home sits on the Chesapeake Bay's South River. It is perfect for a vacation, work/school-fr ...
From $1054 per night (USD)
VRBO
From $160 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 $160 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Belle By the Bay- Great location and parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
As soon as you enter this beautiful two-floor home, you'll be greeted by the modern yet very comfortable open-concept de ...
From $333 per night (USD)
VRBO
$Waterfront Estate w\/ Private Beach + Dock$
From $2280 per night (USD)
Expedia
Waterfront Estate w\/ Private Beach + Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Private Nantucket style waterfront estate w/ beach, deep water slips and a 180 waterview. Expansive western sunsets on F ...
From $2280 per night (USD)
Expedia
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VRBO
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 ...
Click For Pricing
VRBO
From $385 per night (USD)
Expedia
Very nice house on quiet lot, dead end street. Kid friendly neighborhood.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very nice house on quiet lot, dead end street. Kid friendly neighborhood, good bike riding, etc. 3 Bedrooms, sleeps 6. ...
From $385 per night (USD)
Expedia
From $757 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 $757 per night (USD)
VRBO
$Spacious Good-Value Accommodation! w\/ Outdoor Pool, Pet-Friendly, Free Parking$
From $505 per night (USD)
VRBO
Spacious Good-Value Accommodation! w\/ Outdoor Pool, Pet-Friendly, Free Parking
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 $505 per night (USD)
VRBO
From $253 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 $253 per night (USD)
VRBO
$Beach cottage with firepit, grill, outdoor areas, AC, & W\/D$
From $550 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 $550 per night (USD)
Expedia
$Coastal Edgewater Home w\/ Private Hot Tub!$
From $357 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 $357 per night (USD)
VRBO
$Spacious home with an outdoor pool, screened porch, washer\/dryer & central AC$
From $818 per night (USD)
Expedia
Spacious home with an outdoor pool, screened porch, washer\/dryer & central AC
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Thomas Point Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $818 per night (USD)
Expedia
$Waterfront home with spacious deck, dock, washer\/dryer & central AC$
Click For Pricing
VRBO
Waterfront home with spacious deck, dock, washer\/dryer & central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
At Londontown Gardens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
Click For Pricing
VRBO
From $2207 per night (USD)
VRBO
Waterfront Home to Enjoy
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
WATERFRONT — Available commissioning week 2024. Beautiful Nantucket style home right on the South River just 7 miles fro ...
From $2207 per night (USD)
VRBO
From $286 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 $286 per night (USD)
VRBO
From $351 per night (USD)
Expedia
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Bedrooms:
3
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 $351 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront Beach House with amazing views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The perfect place to experience amazing sunrise/sunset views on the water, beach within walking distance, restaurants, d ...
Click For Pricing
VRBO
From $527 per night (USD)
Expedia
Bay Poolhouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Bay Pool House License number 000268 ...
From $527 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $1794 per night (USD)
Expedia
Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger
Bedrooms:
4
Bathrooms:
8
Sleeps:
14
**** 360 Tour ******* https://youriguide.com/7cdq0_3731_thomas_point_rd_annapolis_md Enjoy Annapolis with family & fri ...
From $1794 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $321 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 $321 per night (USD)
Expedia

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Results: 133 Rentals