
Anne Arundel Area Rentals

- From $1645 per night (USD)
VRBO
Cool 1870's home anchored in the Historic District with modern amenities.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Our century-and-a-half-old, five bedroom and three bath home with 3,000 square feet centrally situated in the heart of t ...
From $1645 per night (USD)VRBO
- From $201 per night (USD)
VRBO
“Athens of America,” Annapolis Apartment Two B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $201 per night (USD)VRBO
- From $319 per night (USD)
VRBO
Available for Maryland Legislative Session 2024 ! Perfect location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the essence of Historic Annapolis with this recently renovated Maryland Avenue apartment. Located in the 'Johnson ...
From $319 per night (USD)VRBO
- Click For Pricing
Expedia
Tudor style house near historic downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
A large Tudor style house with plenty of living space; several sitting rooms, a large back porch, an open field and surr ...
Click For PricingExpedia
- From $442 per night (USD)
VRBO
NEW 5 Bedroom Home with Pier by Water
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to this brand-new relaxing home with a pier by the water for your getaway. It is perfect for vacations, retreats ...
From $442 per night (USD)VRBO
- From $142 per night (USD)
Expedia
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Annapolis, where history and nature come together! Make yourself at home in this cozy 1-bedroom, 1-bath cond ...
From $142 per night (USD)Expedia
- From $601 per night (USD)
VRBO
Stay \"Around the corner\" from Annapolis hot spots with new King bed, fenced-in yard and parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly ...
From $601 per night (USD)VRBO
- Click For Pricing
Expedia
A Delight on Dean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sitting on a quiet, tree lined street, this home enjoys being located in the sought after neighborhood of Murray Hill. ...
Click For PricingExpedia
- From $750 per night (USD)
VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $750 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Private Pool Paradise Modest Socials Welcomed
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Beautiful property with spacious home and grounds perfect for a modest get together of friends and family. If you’re int ...
From $1500 per night (USD)VRBO
- From $933 per night (USD)
VRBO
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Sanare Estates! The ultra-private waterfront estate is like your own luxury resort, located on 20+ Acres with ...
From $933 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Walkable Eastport Home with Firepit, Porch & Fenced-in Yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to your home away from home in the heart of the Maritime Republic of Eastport—a vibrant, walkable neighborhood j ...
From $504 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Waterfront Oasis of Annapolis Star
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Studio, furnished apartment above detached garage on family's sprawling property. Queen-bed, with pull out full couch. S ...
From $495 per night (USD)VRBO
- From $329 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 $329 per night (USD)VRBO
- From $197 per night (USD)
VRBO
Guest Quarters at the Inn - 101
- 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 $197 per night (USD)VRBO
- From $92 per night (USD)
VRBO
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore the best of Maryland and book a stay at this cozy 1-bed, 1-bath vacation rental home in Lothian! Nestled on a fa ...
From $92 per night (USD)VRBO
- 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 $525 per night (USD)
VRBO
Delightful little Historic District gem - for the antique lover and history buff.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR21-144963 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $525 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 $613 per night (USD)
VRBO
DOWNTOWN ANNAPOLIS DREAMHOME AWAITS!!! 3 BR charming home sits in the heart of Annapolis within walking distance to all major points of interest AND a Rooftop Deck!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STR-144253 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $613 per night (USD)VRBO
- From $1504 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 $1504 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)
VRBO
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)VRBO
- Click For Pricing
Expedia
Beautiful, clean and Peaceful surrounded by parks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
There is a room to rent in a three level floor beautiful townhome . The bedrooms are on the third floor with a full bat ...
Click For PricingExpedia
- From $287 per night (USD)
VRBO
Spacious Townhouse in the Heart of Washington D.C.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 7
Summary Enjoy a clean, quiet and spacious place to call your home. Best for visiting the landmarks of Washington DC. Loc ...
From $287 per night (USD)VRBO
- From $226 per night (USD)
Expedia
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)Expedia
- From $940 per night (USD)
VRBO
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)VRBO
- From $316 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 $316 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)
VRBO
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)VRBO
- 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
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 ...
Click For PricingVRBO
- From $331 per night (USD)
VRBO
Charming Renovated Historic Home Downtown wparking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Professionally UV sanitized and ozone deep cleaned between guests .Cute and comfortable home in the heart of the HISTORI ...
From $331 per night (USD)VRBO
- 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 ...
Click For PricingExpedia
- From $332 per night (USD)
VRBO
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
A stunning home, “Circa 1885” is a restored piece of Annapolis history. Sitting at one of the two major gateways that l ...
From $332 per night (USD)VRBO
- 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
- Click For Pricing
VRBO
Quiet & Relaxing Waterfront Home Near Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Quiet and Relaxing Waterfront home 5 minutes from Downtown Annapolis. Ideal for Business stays, Relocation Home, Get Tog ...
Click For PricingVRBO
- 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
- Click For Pricing
VRBO
New Listing! Walk to USNA/Capitol/Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Want to enjoy being in downtown Annapolis, but on one of the quieter streets? If that sounds good, this is the place fo ...
Click For PricingVRBO
- From $328 per night (USD)
Expedia
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)Expedia
- From $553 per night (USD)
VRBO
★ 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)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $407 per night (USD)
VRBO
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)VRBO
- From $279 per night (USD)
Expedia
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)Expedia
- From $314 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 $314 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 $848 per night (USD)
VRBO
Quiet Relaxing Waterfront Suisse Chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This spacious, airy and relaxing 3 bedroom house, comes with a beautiful loft and an additional queen pull out sofa be ...
From $848 per night (USD)VRBO
- From $289 per night (USD)
Expedia
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)Expedia
- From $511 per night (USD)
VRBO
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)VRBO
- From $402 per night (USD)
Expedia
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)Expedia
- 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 $263 per night (USD)
Expedia
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 $263 per night (USD)Expedia
- 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
- Click For Pricing
Expedia
Cheerful 1 bedroom w pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy one bedroom with pool outdoor eating space and expansive yard for the kids to play in. Private bedroom, bathroom, a ...
Click For PricingExpedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $771 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 $771 per night (USD)Expedia
- From $562 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 $562 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $311 per night (USD)
VRBO
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)VRBO
- From $766 per night (USD)
Expedia
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)Expedia
- From $656 per night (USD)
VRBO
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)VRBO
- From $634 per night (USD)
Expedia
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)Expedia
- From $761 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 $761 per night (USD)VRBO
- From $803 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 $803 per night (USD)Expedia
- From $295 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 $295 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- 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)
Expedia
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)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- 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