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 $354 per night (USD)
VRBO
★ Odenton Oasis ★ Patio - Central to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our beautifully furnished, colonial-style townhome just minutes from MARC station with great proximity to DC, ...
From $354 per night (USD)
VRBO
From $340 per night (USD)
VRBO
BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
The house is in a quiet residential neighborhood. It has easy access to all major routes: I-97, I-695, I-95, I-295, rout ...
From $340 per night (USD)
VRBO
From $445 per night (USD)
VRBO
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Very cozy bedrooms with two incredible family rooms to enjoy internet tv, game room, built in bar, beautiful screened in ...
From $445 per night (USD)
VRBO
From $554 per night (USD)
Expedia
Stay in Heart of Downtown Annapolis Steps to Main St at Historic Carriage House
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Originally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose ...
From $554 per night (USD)
Expedia
From $716 per night (USD)
VRBO
Waterfront Cheerful 6 BR Home with Private Pier
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Welcome to this brand-new relaxing home with a private pier by the water for your getaway. It is perfect for vacations, ...
From $716 per night (USD)
VRBO
From $982 per night (USD)
VRBO
One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $982 per night (USD)
VRBO
From $1444 per night (USD)
VRBO
Water view from every window - Located at the point where the deep water of Saltworks Creek meets the Severn River.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
STR50082- THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1444 per night (USD)
VRBO
From $1291 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 $1291 per night (USD)
VRBO
From $947 per night (USD)
VRBO
4 BR/3BA home in the heart of Historic Downtown Annapolis. 1 1/2 blocks from the Naval Academy
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-141783 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $947 per night (USD)
VRBO
From $783 per night (USD)
VRBO
Location=AMAZING! Garage Parking for 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $783 per night (USD)
VRBO
From $917 per night (USD)
VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
RENT-005995-2024 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $917 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR- 270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $279 per night (USD)
VRBO
From $466 per night (USD)
VRBO
4 Bedroom/3 Bathroom with parking minutes from downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $466 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Guest quarters at the inn - 205
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Guest Quarters at the Inn is a vacation rental site situated one block from the -Bay in the historic and charming to ...
From $242 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Guest quarters at the inn - 204
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $226 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 $323 per night (USD)
VRBO
Charming cottage with parking. Easy walk to downtown.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street withi ...
From $323 per night (USD)
VRBO
From $162 per night (USD)
Expedia
Chesapeake Bayside Loft
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Recently updated 1 bedroom, 1 bathroom loft studio unit with fully equipped kitchen, Smart TV in bedroom and free high s ...
From $162 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Listing will never be posted on Craig's list - VRBO only **Adorable 1930's cape cod, located in the historic Murray Hill ...
From $493 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $408 per night (USD)
VRBO
Walk to the Chesapeake Bay! Herrington Harbour is a few blocks away.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Walk to Herrington Harbour South, Rose Haven's 2 acre waterfront park or the market, hair salon, bar and restaurant. Th ...
From $408 per night (USD)
VRBO
Click For Pricing
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 $2878 per night (USD)
VRBO
Nantucket on the Chesapeake Heated Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy comfort and convenience in this beautifully-appointed home! Nantucket on the Chesapeake has an old-world feel yet ...
From $2878 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City ...
From $448 per night (USD)
Expedia
From $971 per night (USD)
VRBO
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
This 4 BR, 4.5 BA house is perfect for entertaining your guests! Come into our spacious open floor plan. You feel li ...
From $971 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Walk to Beach! King Bed & Free Beach Passes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that o ...
From $346 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Cozy Cottage 3 beds 2 baths W/ Outdoor grill!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Lovely updated 3 bedroom 2 bathroom cottage walking distance to restaurants, shopping and the beach. Nicely decorated ho ...
From $269 per night (USD)
VRBO
From $1081 per night (USD)
Expedia
Parking for days at the unique Deep in the Heart of Annapolis with large private deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been ...
From $1081 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Historic Annapolis Home 1.5 blocks from center of town.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractio ...
From $328 per night (USD)
VRBO
From $553 per night (USD)
Expedia
★ Midcentury Modern Getaway ★ Prime Location ★
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this complet ...
From $553 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 $407 per night (USD)
Expedia
Nice 5 BDR / 3 BATH Home near BWI Airport with WIFI, Beach, Parking, Ambiance
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Business, Govt. or family trip? Riviera Beach welcomes you to this lovely, elegant, well-lit and sanitized 5 BD/3 BATH h ...
From $407 per night (USD)
Expedia
From $279 per night (USD)
VRBO
New Downtown Annapolis Condo With Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No ...
From $279 per night (USD)
VRBO
From $975 per night (USD)
Expedia
West Annapolis Cottage
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: Recently renovated, this is the perfect location for your family & friends to enjoy Naval Academy events, boat ...
From $975 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Modern three-bedroom, two full bath home with half-bath and new furnishings. Quiet neighborhood easily accessible to Sa ...
From $289 per night (USD)
VRBO
From $511 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 $511 per night (USD)
Expedia
From $402 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 $402 per night (USD)
VRBO
From $638 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 $638 per night (USD)
VRBO
From $268 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 $268 per night (USD)
VRBO
From $314 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 $314 per night (USD)
VRBO
From $875 per night (USD)
VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
From $875 per night (USD)
VRBO
From $437 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 $437 per night (USD)
Expedia
From $670 per night (USD)
VRBO
Steps to USNA and Main St with Private Patio and Parking at Historic Gem
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovat ...
From $670 per night (USD)
VRBO
From $225 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 $225 per night (USD)
VRBO
From $657 per night (USD)
VRBO
Stylish Midcentury Ranch Pet-Friendly Home Just 1.5 Miles from Navy Stadium One-Level Living
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Stylish Midcentury Ranch Just 1.5 Miles from Navy Stadium! This beautifully renovated 4BR/2BA home is perfectly located ...
From $657 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Historic Downtown Union House with Free Off-Site Parking & Private Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly res ...
From $524 per night (USD)
Expedia
From $502 per night (USD)
VRBO
💥Your Annapolis Retreat near the beach and downtown💥
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Welcome to our recently renovated retreat in Annapolis. The place is located minutes from downtown, in the neighborhood ...
From $502 per night (USD)
VRBO
From $471 per night (USD)
Expedia
Cozy Annapolis Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stay in the heart of Annapolis. Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly r ...
From $471 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Club Carp North Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Renovated throughout with three bedrooms and two full baths. This kid-friendly home has a large fenced yard with a swing ...
From $305 per night (USD)
VRBO
From $631 per night (USD)
Expedia
Large Home with Pool & 7 bedrooms; sleeps 21
Bedrooms:
2
Bathrooms:
7
Sleeps:
16
Relax at this large 7-bedroom spacious top-quality home that is ideal for large gatherings where all can be together in ...
From $631 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located on Meridith Creek, which flows out to Whitehall and Chesapeake Bays, this charming vacation rental features a la ...
From $349 per night (USD)
VRBO
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Expedia
New Townhome/Room!!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Owner and dog live in townhome. Seeking short rentals only. Spacious one bedroom with private bath for professionals see ...
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Expedia
From $771 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 $771 per night (USD)
VRBO
From $562 per night (USD)
Expedia
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 $562 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy family-home in the woods, 10 min to Naval Academy!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Embed yourself in the quietness of the woods and birds singing. Our backyard has the 5th largest tree of its species in ...
Click For Pricing
VRBO
From $311 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 $311 per night (USD)
Expedia
From $766 per night (USD)
VRBO
Eastport Historic Firehouse with Parking, Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in ...
From $766 per night (USD)
VRBO
From $656 per night (USD)
Expedia
Parking & Pet Friendly USNA-themed Annapolis home
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This Naval Academy-themed 3 Bedroom home was just fully renovated and is ready to host Annapolis visitors! There are mul ...
From $656 per night (USD)
Expedia
From $634 per night (USD)
VRBO
Waterfront Home with Stunning Views, Pool, Pier & Parking Mins to Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to this beautiful waterfront home in the quiet Cool Spring Cove of the Magothy River in Arnold, MD. Not only do ...
From $634 per night (USD)
VRBO
From $761 per night (USD)
Expedia
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 $761 per night (USD)
Expedia
From $803 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 $803 per night (USD)
VRBO
From $295 per night (USD)
Expedia
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 $295 per night (USD)
Expedia
Click For Pricing
VRBO
Chic Condo w/ Balcony in the Heart of Annapolis!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
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VRBO
From $563 per night (USD)
VRBO
The Liberty House- Pristine Renovation with parking
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Liberty House ! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat ...
From $563 per night (USD)
VRBO
From $1497 per night (USD)
VRBO
Riverfront Retreat 7mil from MD Renaissance Fest!
Bedrooms:
6
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 $1497 per night (USD)
VRBO
From $598 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 $598 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Charming Historic Townhouse Steps From USNA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bath ...
From $303 per night (USD)
VRBO
From $233 per night (USD)
Expedia
The Blue Crab Beach House - Free beach passes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to The Blue Crab just a few blocks from the Chesapeake Bay. You will enjoy staying at our newly renovated luxury ...
From $233 per night (USD)
Expedia
From $1175 per night (USD)
VRBO
Waterfront, Dock, Private Pool ~ Weekly & Monthly Rentals available!
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 $1175 per night (USD)
VRBO
From $997 per night (USD)
VRBO
Annapolis Waterfront home with incredible views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Annapolis waterfront property with stunning views of the Chesapeake bay, Gibson and Dobbins Islands, and the wide open M ...
From $997 per night (USD)
VRBO
From $360 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 $360 per night (USD)
VRBO
From $665 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 $665 per night (USD)
Expedia
From $559 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 $559 per night (USD)
VRBO
From $496 per night (USD)
Expedia
Hot Tub Haven: Cozy Annapolis Backyard Oasis!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A serene escape awaits you at our cozy 4-bedroom, 2.5 bath retreat! We are just minutes away from Historic Downtown Anna ...
From $496 per night (USD)
Expedia
From $841 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 $841 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Annapolis Downtown Entire Townhome 3 bed 6 guests
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while stayin ...
From $413 per night (USD)
Expedia
From $383 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 $383 per night (USD)
VRBO
From $1267 per night (USD)
Expedia
Parking at Randall House Across from USNA Gate 1
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1267 per night (USD)
Expedia
From $1116 per night (USD)
VRBO
Sprawling Luxury Home on a Private Cul De Sac with Gaming Sports Bar, Big Yard Mins to Annapolis
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Spacious custom home - Perfect for Naval Academy families and long visits to Annapolis Enjoy your stay in this expansive ...
From $1116 per night (USD)
VRBO
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Expedia
5 BDRM across from the USNA Stadium
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
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Expedia
From $1799 per night (USD)
VRBO
Stunning Waterfront Home in Round Bay with multiple living spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Available for Boat Shows! Ask us about the option to add on the 5th bedroom. This beautiful home with unobstructed view ...
From $1799 per night (USD)
VRBO
From $295 per night (USD)
Expedia
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 $295 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Adorable home steps from Navy Stadium!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Can’t beat the space and location of this property for your trip to Annapolis! Just a block away from Navy Stadium for a ...
From $376 per night (USD)
VRBO
From $197 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 $197 per night (USD)
VRBO
From $160 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 $160 per night (USD)
VRBO
From $52 per night (USD)
Expedia
Great BEDROOM in a townhouse in the heart of Hanover.
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Hello, you will be renting a private bedroom in a Very clean and quiet home Spacious living room and dining room Grea ...
From $52 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Chase Creek Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $420 per night (USD)
VRBO
From $1256 per night (USD)
Expedia
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
Bedrooms:
5
Bathrooms:
6
Sleeps:
15
Bella Chateau Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1256 per night (USD)
Expedia
From $805 per night (USD)
VRBO
Updated historic home with parking; near Academy, college & harbor - central AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Anchors Aweigh Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $805 per night (USD)
VRBO
From $793 per night (USD)
Expedia
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The Ship's Bridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $793 per night (USD)
Expedia
From $759 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 $759 per night (USD)
VRBO
Click For Pricing
Expedia
Beach House (Annapolis) Bay Ridge Community
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Relax on the front porch while enjoying sweeping views of the Chesapeake Bay. Enjoy the beach right in front of house. P ...
Click For Pricing
Expedia
From $1024 per night (USD)
VRBO
Private Pier Waterfront Jolly Roger mins to DTA
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is o ...
From $1024 per night (USD)
VRBO
From $573 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 $573 per night (USD)
Expedia
From $257 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 $257 per night (USD)
VRBO
$Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis\n$
From $652 per night (USD)
VRBO
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis\n
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 $652 per night (USD)
VRBO
From $327 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 $327 per night (USD)
VRBO
From $499 per night (USD)
Expedia
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 $499 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Stay mins to downtown in sunny fenced-in backyard in waterfront community Pet-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Still available for Commissioning Week 2025! Just minutes from Downtown Annapolis, this charming rambler is located in ...
From $505 per night (USD)
VRBO
From $494 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 $494 per night (USD)
Expedia

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Results: 622 Rentals