Anne Arundel Area, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anne Arundel Area, Maryland on RentalSaver.com!

Anne Arundel Area Rentals

From $483 per night (USD)
VRBO
Harbor Breezes at Herrington Harbor
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
If you are looking for a comfortable and clean home for your stay while visiting Herrington Harbor, our beaches or other ...
From $483 per night (USD)
VRBO
From $578 per night (USD)
VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $578 per night (USD)
VRBO
From $369 per night (USD)
VRBO
Annapolis Garden Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our little oasis! We're tucked away on a beautiful residential street yet 7 minutes away from restaurants, co ...
From $369 per night (USD)
VRBO
From $437 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 $437 per night (USD)
VRBO
From $169 per night (USD)
VRBO
The Heron's Nest at Atlantic Marina
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Bay breezes and magnificent views make this quaint cottage the perfect getaway! Only steps away from the beach, this r ...
From $169 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $494 per night (USD)
Expedia
From $654 per night (USD)
VRBO
Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Take a stroll along the brick-lined sidewalks of P ...
From $654 per night (USD)
VRBO
From $322 per night (USD)
VRBO
Annapolis Tree House Apartment- luxury shower, separate space
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of lan ...
From $322 per night (USD)
VRBO
From $603 per night (USD)
VRBO
Historic Annapolis Union House with Private Patio & Free Off-Site Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy Annapolis, MD in this charming Federal-style ...
From $603 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Waterfront River Cottage for 2, dog-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the Difference: Professionally Managed by iTrip Annapolis This adorable cottage sits on 3 picturesque acres ...
From $364 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Your Annapolis Retreat near the Naval Academy and downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Welcome to our retreat in Annapolis. The place is located minutes from downtown and the Naval Academy, in the neighborho ...
From $524 per night (USD)
VRBO
From $956 per night (USD)
Expedia
Large Home w/ Private Pool, Gym, Sauna, 7 Bedrooms, Sleeps 21
Bedrooms:
2
Bathrooms:
7
Sleeps:
16
Relax at this spacious 4,125 sqft, top-quality home on 1 acre. This 7-bedroom, 2.5 bathroom home features a private pool ...
From $956 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Waterfront Annapolis Cottage: Fire Pit & Pier
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Located on Meridith Creek, this charming vacation rental features a large yard, fishing pier, and an outdoor space with ...
From $367 per night (USD)
VRBO
From $904 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 $904 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Recently Renovated Annapolis Home - Conveniently Located
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walk ...
From $465 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Spectacular Location: State Circle Apartment
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapol ...
From $539 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Deluxe Basement Guest Suite w/ Luxury Amenities Minutes From BWI/Annapolis/DC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to a luxurious retreat in Odenton. Boasting a stylish 2-bed design, stainless steel appliances, a rainfall shower ...
From $233 per night (USD)
VRBO
From $343 per night (USD)
Expedia
CHeerful 3-bedroom waterfront home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to this relaxing home by the water for your getaway with private pier.It is perfect for vacations, retreats, mee ...
From $343 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Eastport Historic Firehouse with Parking, Dogs OK
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis This is a unique home like none other in downtown ...
From $613 per night (USD)
VRBO
From $821 per night (USD)
Expedia
Waterfront Home w Pool, Pier & Parking Mins to Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this beautiful waterfront home in the q ...
From $821 per night (USD)
Expedia
From $764 per night (USD)
VRBO
The Santi Paradise
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
If you looking for a unique place to stay come to THE SANTI PARADISE. We value you as our guest and are committed to you ...
From $764 per night (USD)
VRBO
From $980 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 $980 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Annapolis Condominium in the heart of the historic center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $383 per night (USD)
VRBO
From $1585 per night (USD)
Expedia
Riverfront Retreat 7mil from MD Renaissance Fest!
Bedrooms:
5
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 $1585 per night (USD)
Expedia
From $728 per night (USD)
VRBO
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
Chesapeake Paradise (`The Paradise`) is a stunning, recently remodeled, luxurious, two-story 6+ bedroom 4 bath waterfron ...
From $728 per night (USD)
VRBO
From $478 per night (USD)
VRBO
Historic Renovated Home in the Heart of Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to our listing on East Street. Located in the heart of downtown our front porch sits in the shade of the iconic ...
From $478 per night (USD)
VRBO
From $414 per night (USD)
VRBO
The Very Best location - 50 Steps from Main Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Truly in the HEART of downtown we are 50 steps from Main Street, City Dock and all the action. Featuring the best front ...
From $414 per night (USD)
VRBO
From $1350 per night (USD)
VRBO
Waterfront Home, Dock, Private Pool & Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Fantastic location, minutes from Annapolis by land or water. Amazing sunrises and sunsets can be seen sitting in an Adi ...
From $1350 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Waterfront North Beach Home ~ 2 Mi to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Highlighted by its coastal charm and scenic location, this well-appointed North Beach home is well-suited for small grou ...
From $531 per night (USD)
VRBO
From $638 per night (USD)
Expedia
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Our tastefully appointed cottages sit on almost an acre of waterfront land. Peaceful and tranquil, yet close to shops an ...
From $638 per night (USD)
Expedia
From $702 per night (USD)
VRBO
All-stop. Rental Midships.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome ste ...
From $702 per night (USD)
VRBO
From $560 per night (USD)
VRBO
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A serene escape awaits you at our cozy 4-bedroom, 2.5 bath retreat! We are just minutes from Historic Downtown Annapolis ...
From $560 per night (USD)
VRBO
From $1095 per night (USD)
VRBO
Newer Waterfront Home on the Chesapeake Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
2021 built waterfront home with sweeping views of the Chesapeake Bay located on a quiet, private road in the community o ...
From $1095 per night (USD)
VRBO
From $459 per night (USD)
Expedia
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 $459 per night (USD)
Expedia
From $882 per night (USD)
VRBO
Parking at Randall House Across from USNA Gate 1
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Experience the Difference: Professionally Managed by iTrip Annapolis The Randall House is an historic gem in the heart ...
From $882 per night (USD)
VRBO
From $857 per night (USD)
Expedia
Sprawling Luxury Home on a Private Cul De Sac with Gaming Sports Bar, Big Yard Mins to Annapolis
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Experience the Difference: Professionally Managed by iTrip Annapolis Spacious custom home - Perfect for Naval Academy f ...
From $857 per night (USD)
Expedia
From $1752 per night (USD)
VRBO
Stunning Waterfront Home in Round Bay with multiple living spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Experience the Difference: Professionally Managed by iTrip Annapolis Available for Boat Shows! Ask us about the option ...
From $1752 per night (USD)
VRBO
From $2786 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 $2786 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Lovely home in a great neighborhood!! Private entrance. Excellent location. Brand New 2,300 Sq. ft 3 bedroom basement ap ...
From $381 per night (USD)
VRBO
From $255 per night (USD)
VRBO
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic ...
From $255 per night (USD)
VRBO
From $244 per night (USD)
VRBO
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to this beautiful three-bedroom, two full bath, and one half bath home located in the tranquil community of Crof ...
From $244 per night (USD)
VRBO
From $1016 per night (USD)
Expedia
Private Pier Waterfront Jolly Roger mins to DTA
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Experience the Difference: Professionally Managed by iTrip Annapolis Arrive by car or boat to this waterfront home, loc ...
From $1016 per night (USD)
Expedia
From $773 per night (USD)
VRBO
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 $773 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This spacious, well-appointed 1 bedroom, 1 European style bath 2nd floor apartment is in the heart of Eastport. You’ll b ...
From $352 per night (USD)
VRBO
From $732 per night (USD)
VRBO
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
BOOK YOUR ANNAPOLIS VACATION AT BURLEY CREEK HIDEAWAY! Charming home owned by USNA grads. Lovely waterfront two-level ...
From $732 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Walk to all Annapolis has to offer, once parked you’ll never need a car. Walk to City Dock, marinas, restaurants, pubs ...
From $371 per night (USD)
VRBO
From $491 per night (USD)
VRBO
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Charming private space in a quiet neighborhood. Live like locals and enjoy walking or biking around town. Free street p ...
From $491 per night (USD)
VRBO
From $601 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 $601 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Charm & Style in this Renovated Eastport Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Brid ...
From $596 per night (USD)
VRBO
From $647 per night (USD)
Expedia
Historic Chapel Views, Steps to USNA Gate 1 w Private Patio & Off-Site Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Experience the Difference: Professionally Managed by iTrip Annapolis When the owners decided to find their Annapolis ho ...
From $647 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Chesapeake Bay Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
In less than an hour from the D.C. Metro area you're transported to your own private shore on the Chesapeake Bay. This ...
From $395 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Truly Waterfront Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cute cottage tucked away amongst the trees on Stoney Creek in Pasadena Md. Enjoy bird watching from the upper deck just ...
From $272 per night (USD)
VRBO
From $790 per night (USD)
VRBO
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 $790 per night (USD)
VRBO
Click For Pricing
Expedia
Your Annapolis Adventure Starts Here!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
Click For Pricing
Expedia
From $229 per night (USD)
VRBO
Romantic Two Bedroom Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience the best of both worlds at this fully renovated two-bedroom, one-bath, one-level condo located in the tranqui ...
From $229 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Sunny Glen Burnie Home - On-Site Water Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Whether you fancy city life or lake living, this Glen Burnie home has it all! Equipped with 3 bedrooms, 2 bathrooms, and ...
From $396 per night (USD)
Expedia
From $633 per night (USD)
VRBO
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $633 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Idyllic Pasadena Retreat with Garden + Hot Tub!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Plan your trip to the Baltimore suburbs when you book this whimsical getaway in Pasadena! Situated 20 miles from the hea ...
From $361 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Downtown furnished apartment - walking distance to restaurants
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Church owned 2nd Floor apartment in historic house - fully furnished - eat-in kitchen, dining room and living room - has ...
From $351 per night (USD)
VRBO
From $518 per night (USD)
Expedia
Go Navy! Steps to USNA, City Dock & Street Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Experience the Difference: Professionally Managed by iTrip Annapolis Stay in the heart of Historic Annapolis just steps ...
From $518 per night (USD)
Expedia
From $625 per night (USD)
VRBO
Historic Hanover House Across from USNA Gate 3 w Private Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis The fully-renovated 1800 historic home is just ste ...
From $625 per night (USD)
VRBO
From $227 per night (USD)
Expedia
Tranquility Awaits
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Entire Guest House. One bedroom, one bathroom with loft. Three beds, queen, full and twin. Full kitchen, laundry, dedi ...
From $227 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Bay View Studio Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $388 per night (USD)
VRBO
From $1016 per night (USD)
Expedia
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Bedrooms:
4
Bathrooms:
7
Sleeps:
15
Home is clean, spacious, and well-maintained, designed for comfort and convenience. Located in a safe residential neighb ...
From $1016 per night (USD)
Expedia
From $1201 per night (USD)
VRBO
USNA Stay w Private Pool, Hot Tub, King Beds, Child Safe & Stocked, Pet Friendly
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
USNA Family Stay w/Pool - Infant/Toddler Friendly! New in 2026: Blue and Gray Bedding Themes, NEW 8 Person Hot Tub, More ...
From $1201 per night (USD)
VRBO
From $532 per night (USD)
VRBO
ACROSS FROM STADIUM - walk to downtown Annapolis.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $532 per night (USD)
VRBO
From $935 per night (USD)
VRBO
Serene Sunsets at Historic Waterfront Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy stunning western-facing views across the riv ...
From $935 per night (USD)
VRBO
From $547 per night (USD)
VRBO
Gem in Downtown Annapolis, close to USNA, St. John's College
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryla ...
From $547 per night (USD)
VRBO
From $890 per night (USD)
VRBO
Prime Location Modern Comfort 1 Block to Gate 1 w Bar & Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Modern Elegance in Historic Annapolis ...
From $890 per night (USD)
VRBO
From $614 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 $614 per night (USD)
Expedia
From $716 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $716 per night (USD)
VRBO
From $707 per night (USD)
Expedia
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfec ...
From $707 per night (USD)
Expedia
From $417 per night (USD)
VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $417 per night (USD)
VRBO
From $584 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 $584 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Beautiful waterfront property with a private beach and dock thirty minutes from Annapolis. Perfect for family reunions o ...
From $545 per night (USD)
VRBO
From $951 per night (USD)
VRBO
Annapolis Entertainment Complex
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This gorgeous four bedroom four bathroom home in Arnold that sleeps 10 is perfect for entertaining while you’re in Annap ...
From $951 per night (USD)
VRBO
From $571 per night (USD)
VRBO
Chesapeake Paradise LITE 4+br3ba Peaceful Watrfrnt
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This is a fabulous 4-5 bedroom 3-ba House, affectionately called Porchlandia, with spectacular views on a lush, waterfro ...
From $571 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Stunning Waterfront Cottage in the Sailing Capital of the World!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience an exceptional waterfront setting in the Sailing Capital of the World. This upgraded 2‑bedroom, 1‑bath cottag ...
From $574 per night (USD)
VRBO
From $638 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 Bed/2 Bath Apartment with additional family room with brand new queen sleeper sofa in Historic Downtown Annapolis step ...
From $638 per night (USD)
VRBO
From $2274 per night (USD)
Expedia
Waterfront Home near Annapolis, MD
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Beautiful waterfront home built in 2013 located on 75 acres of picturesque farmland. Exceptional, award-winning architec ...
From $2274 per night (USD)
Expedia
From $950 per night (USD)
VRBO
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Conveniently located just 4.5 miles from historic Annapolis the Coastie Cottage is the perfect homebase for your next vi ...
From $950 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape the city hustle to relax on the Chesapeake! Savor our three-bedroom Cottage in this peaceful western shore spot w ...
From $326 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. We feature a main level open floor plan ...
From $668 per night (USD)
VRBO
From $549 per night (USD)
Expedia
PERFECT LOCATION in the heart of history
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front d ...
From $549 per night (USD)
Expedia
From $629 per night (USD)
VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Skridt fra Annapolis By Dock og US Naval Academy- gåtur til alle butikker, restauranter og downtown begivenheder. Denne ...
From $629 per night (USD)
VRBO
From $842 per night (USD)
VRBO
Waterfront - Wonderful View, Spacious, Relaxing, Lovely Front Porch and Deck
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy a beautiful spacious 5 bedroom 3.5 bath home in a quiet setting overlooking the Magothy River. The home includes t ...
From $842 per night (USD)
VRBO
From $579 per night (USD)
VRBO
Heart of Historic District!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the Cit ...
From $579 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Beautiful Condo - Water View Near City Dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $302 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Pristine Downtown 1-Bedroom Steps from State House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minute ...
From $315 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...
From $470 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to your own private spa retreat just minutes from Downtown Annapolis. This quiet loft studio is designed for tota ...
From $268 per night (USD)
VRBO
From $646 per night (USD)
Expedia
USNA Home Steps to Stadium Dog-Friendly w Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Experience the Difference: Professionally Managed by iTrip Annapolis In Navy jargon, the goat locker is a lounge, sleep ...
From $646 per night (USD)
Expedia
From $1577 per night (USD)
VRBO
Annapolis Bayfront Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Beautifully restored turn of the century beach cottage located on an acre of landscaped property with magnificent views ...
From $1577 per night (USD)
VRBO
From $111 per night (USD)
Expedia
Lower Level Loft - Adorable Studio Apt. Near BWI
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Kick back and relax in this calm, stylish space. Newly updated in-law suite with private entrance & outdoor space on bo ...
From $111 per night (USD)
Expedia
From $536 per night (USD)
VRBO
West River Waterfront Escape with Boat Lift, Kayaks & Bay Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Waterfront West River Retreat with Private Pier, Kayaks & Chesapeake Bay Views Enjoy the best of Maryland waterfront li ...
From $536 per night (USD)
VRBO
From $1215 per night (USD)
VRBO
42 Acres of Serenity & Nature Just 15 Miles To Annapolis
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Hole In the Wall Farm I is a large open concept home situated on 42 picturesque acres just 15 minutes from Annapolis. I ...
From $1215 per night (USD)
VRBO
From $945 per night (USD)
VRBO
Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Naptown Nook, conveniently located in d ...
From $945 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Updated North Beach Cottage: Pet Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Step into this charming coastal cottage and let North Beach welcome you to a relaxing getaway! The 3-bedroom, 2-bathroom ...
From $288 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Large 2 bedroom house with private parking in a nice neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Bring the whole family to this great private duplex with lots of room for fun. You will be close to many attractions. Lo ...
From $333 per night (USD)
VRBO
Click For Pricing
Expedia
MODERN 2022 NEWLY BUILT TOWNHOME
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...
Click For Pricing
Expedia

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Results: 682 Rentals