Anne Arundel Area Rentals
From $335 per night (USD)VRBO
\"La Licorne\" Waterfront Beach Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to "La Licorne" Waterfront Beach Cottage Escape to our cozy beachfront cottage, a perfect getaway for families ...
From $335 per night (USD)VRBO
From $1270 per night (USD)Expedia
Waterfront- 5-bedroom house with dock in charming North Beach
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 18
Experience an unforgettable vacation in this newly listed waterfront 5-bedroom house. This beautiful property offers ple ...
From $1270 per night (USD)Expedia
From $278 per night (USD)VRBO
Adorable 1 bedroom apartment in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Enjoy a stylish experience at this centrally-located apartment. 2 minute walk to Main Street and all of the att ...
From $278 per night (USD)VRBO
From $380 per night (USD)VRBO
2 Bedroom Renovated Condo in Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Newly renovated 2 bedroom apartment in downtown Annapolis. Steps from Main Street and all that Annapolis has to ...
From $380 per night (USD)VRBO
From $660 per night (USD)VRBO
Downtown Annapolis Gem: 3BR\/2BA
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to our newly renovated 3BR/2BA apartment in downtown Annapolis! With two king beds, one queen bed, and ...
From $660 per night (USD)VRBO
From $257 per night (USD)VRBO
1 room with additional amazing sunroom
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 3
Summary: Enjoy a wonderful experience at this centrally-located apartment. 2 minute walk to Main Street and all of the a ...
From $257 per night (USD)VRBO
From $236 per night (USD)VRBO
Lovely 1 bedroom apartment in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Summary: Keep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to off ...
From $236 per night (USD)VRBO
From $222 per night (USD)VRBO
Charming 4-bedroom townhome with WiFi and AC in lovely Odenton.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the beauty of Odenton from this marvelous 4-bedroom townhome. With a king bed, full bed, and twin bed, guests w ...
From $222 per night (USD)VRBO
From $673 per night (USD)VRBO
Private 4-bedroom house in Annapolis, great location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Your home away from home in Annapolis with 4 bedrooms. Under 2 miles to the Naval Academy! This spacious home is located ...
From $673 per night (USD)VRBO
From $884 per night (USD)VRBO
6 bedroom waterfront home minutes from Downtown Annapolis! Pontoon and jet ski
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Nestled on the Magothy River in Arnold. We are minutes away from all that Annapolis has to offer, with Navy football and ...
From $884 per night (USD)VRBO
From $918 per night (USD)VRBO
Magnolia Harbor Retreat - 4 BR\/3BA HISTORIC DOWNTOWN ANNAPOLIS- QUIET STREET
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RENT-001081-2024 - THIS PROPERTY IS MANAGED BY ANNAPOLIS ACCOMMODATION. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM ...
From $918 per night (USD)VRBO
From $995 per night (USD)VRBO
Stunning Home Nestled on the Peninsula of Eastport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom Annapolis home is an absolute gem, especially with off-street parking! The Craftsman style architecture a ...
From $995 per night (USD)VRBO
From $734 per night (USD)VRBO
Restriction Retreat - Relax & walk to Main St
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $734 per night (USD)VRBO
From $619 per night (USD)VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $619 per night (USD)VRBO
From $781 per night (USD)VRBO
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 $781 per night (USD)VRBO
From $940 per night (USD)Expedia
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $940 per night (USD)Expedia
From $632 per night (USD)VRBO
Waterfront - Wonderful View, Spacious, Relaxing, Lovely Front Porch and Deck
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy a beautiful spacious 5 bedroom 3.5 bath home in a quiet wooded setting overlooking the Magothy River. The home inc ...
From $632 per night (USD)VRBO
From $513 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 $513 per night (USD)VRBO
From $720 per night (USD)VRBO
A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A perfect spot for relaxing, reading, and writing, or as a home-base for visiting the many cultural and natural attracti ...
From $720 per night (USD)VRBO
From $475 per night (USD)VRBO
Stunning Waterfront Cottage with Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $475 per night (USD)VRBO
From $489 per night (USD)VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
2 Bed/2 Bath Apartment in Historic Downtown Annapolis steps away from the main entrance of the Naval Academy. Upstairs ...
From $489 per night (USD)VRBO
From $1901 per night (USD)Expedia
New 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 $1901 per night (USD)Expedia
From $855 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 $855 per night (USD)VRBO
From $355 per night (USD)Expedia
Watrfnt Cottage @ChesapeakeParadise Kayaks\/Dogs OK
- Bedrooms:
- 2
- 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 $355 per night (USD)Expedia
From $1077 per night (USD)VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. With 4 bedrooms and an open studio spac ...
From $1077 per night (USD)VRBO
From $460 per night (USD)Expedia
PERFECT LOCATION in the heart of history
- Bedrooms:
- 3
- 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 $460 per night (USD)Expedia
From $362 per night (USD)VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $362 per night (USD)VRBO
From $498 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 $498 per night (USD)VRBO
From $542 per night (USD)VRBO
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Beautiful waterfront property with a private beach and dock thirty minutes from Annapolis. Perfect for family reunions o ...
From $542 per night (USD)VRBO
From $769 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 $769 per night (USD)VRBO
From $418 per night (USD)VRBO
5-years young STUNNING home with water view!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
5-years-young STUNNING home with OPEN concept, soaring ceilings, hardwoods, gas fireplace, separate laundry room, backya ...
From $418 per night (USD)VRBO
From $406 per night (USD)VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 2
- 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 $406 per night (USD)VRBO
From $651 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 $651 per night (USD)VRBO
From $1133 per night (USD)VRBO
USNA Stay w\/ Private Pool, Indoor Soft Hot Tub, King Beds, & CHILD FRIENDLY GEAR
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
USNA Family Stay w/Pool - Infant/Toddler Friendly! Enjoy the newest addition to my “Family Friendly Staycation” home ho ...
From $1133 per night (USD)VRBO
From $866 per night (USD)VRBO
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 15
Home is clean, spacious, and well-maintained, designed for comfort and convenience. Located in a safe residential neighb ...
From $866 per night (USD)VRBO
From $359 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 $359 per night (USD)VRBO
Click For PricingVRBO
House of Cardz- comforts of home by LLOYD SUITES
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
SUMMARY We are pleased to bring you the "House of Cardz". This is our newest listing since launching the popular "Whiske ...
Click For PricingVRBO
From $245 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 $245 per night (USD)VRBO
From $766 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 $766 per night (USD)VRBO
From $380 per night (USD)VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $380 per night (USD)VRBO
From $616 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 $616 per night (USD)VRBO
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
From $832 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 $832 per night (USD)VRBO
From $316 per night (USD)VRBO
Annapolis-Eastport Cottage Home w\/ RV Van Parking & Hook-up too!
- Bedrooms:
- 2
- 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 $316 per night (USD)VRBO
From $160 per night (USD)VRBO
Hanover!!! Full blast of Fun! Relax and Enjoy!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The property features coffee/tea in a common area, a seasonal outdoor pool, and a business center. Free WiFi in public a ...
From $160 per night (USD)VRBO
From $884 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 $884 per night (USD)VRBO
From $448 per night (USD)VRBO
Location Location Location!!!50 Steps from Main Street and all of the action
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We welcome you to check out our newest listing in the heart of the Historic District with the BEST front porch in downto ...
From $448 per night (USD)VRBO
From $717 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 $717 per night (USD)Expedia
From $608 per night (USD)VRBO
All-stop. Rental Midships.
- Bedrooms:
- 3
- 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 $608 per night (USD)VRBO
From $218 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 $218 per night (USD)VRBO
From $136 per night (USD)VRBO
Quality and Dependable!! 2 Double Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
You’ll find our guest rooms spacious, affordable and comfortable. Whether your tucking into our huge beds and soft beddi ...
From $136 per night (USD)VRBO
From $197 per night (USD)VRBO
Free Breakfast Buffet! Pool | Staybridge Near BWI Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your next trip starts with a stay in our suite! The BWI Airport is just 2 miles away, and there is a complimentary 24-ho ...
From $197 per night (USD)VRBO
From $198 per night (USD)VRBO
Shared Pool. Near BWI Airport!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your next trip starts with a stay in our suite! The BWI Airport is just 2 miles away, and there is a complimentary 24-ho ...
From $198 per night (USD)VRBO
From $996 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 $996 per night (USD)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 $1891 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 $1891 per night (USD)Expedia
From $955 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 $955 per night (USD)VRBO
From $640 per night (USD)Expedia
Recently Renovated Annapolis Home - Conveniently Located
- Bedrooms:
- 3
- 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 $640 per night (USD)Expedia
From $627 per night (USD)VRBO
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to East Street ! We invite you come spend some time at our gorgeous large home in the heart of the Historic Dist ...
From $627 per night (USD)VRBO
From $432 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 $432 per night (USD)Expedia
From $465 per night (USD)VRBO
River Cottage with Beach and Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Get away from the city to this charming cottage on the West River- a calm inlet right off the Chesapeake Bay. Crab or fi ...
From $465 per night (USD)VRBO
From $245 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 n ...
From $245 per night (USD)Expedia
From $1318 per night (USD)VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
From $1318 per night (USD)VRBO
From $635 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 $635 per night (USD)VRBO
From $817 per night (USD)VRBO
Quiet Relaxing Waterfront Suisse Chalet
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This spacious, airy and relaxing 3 bedroom house, comes with a beautiful loft and an additional queen pull out sofa be ...
From $817 per night (USD)VRBO
From $669 per night (USD)Expedia
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 $669 per night (USD)Expedia
From $604 per night (USD)VRBO
★ Midcentury Modern Getaway ★ Prime Location ★
- Bedrooms:
- 3
- 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 $604 per night (USD)VRBO
From $499 per night (USD)VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
- Bedrooms:
- 2
- 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 $499 per night (USD)VRBO
From $395 per night (USD)VRBO
Fleet St Retreat in Downtown- Great Location !
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
We welcome you to our brand new renovation on Fleet Street . Purchased in 2016 this house was taken down to the studs so ...
From $395 per night (USD)VRBO
From $520 per night (USD)Expedia
Steps to Naval Academy, City Dock, and State House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Located in the heart of downtown Annapolis! Walk to Naval Academy, St. John's College, State House, City Dock, Yacht Clu ...
From $520 per night (USD)Expedia
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 $405 per night (USD)VRBO
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $405 per night (USD)VRBO
From $2907 per night (USD)VRBO
Nantucket on the Chesapeake Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy comfort and convenience in this beautifully-appointed home! Nantucket on the Chesapeake has an old-world feel yet ...
From $2907 per night (USD)VRBO
From $133 per night (USD)Expedia
Private detached 1bedroom guest house.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Just few miles away from Baltimore downtown, Ft Meade, NSA, Annapolis and Washington DC. Less than 5 miles away from BWI ...
From $133 per night (USD)Expedia
Click For PricingVRBO
Quiet & Relaxing Waterfront Home Near Annapolis
- Bedrooms:
- 3
- 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 $629 per night (USD)VRBO
Charming Renovated Historic Home Downtown wparking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Professionally UV sanitized and ozone deep cleaned between guests .Cute and comfortable home in the heart of the HISTORI ...
From $629 per night (USD)VRBO
From $425 per night (USD)VRBO
Welcome Aboard the Kathleen Marie!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annap ...
From $425 per night (USD)VRBO
From $429 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 $429 per night (USD)VRBO
From $294 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 $294 per night (USD)VRBO
From $1133 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 $1133 per night (USD)Expedia
From $1064 per night (USD)VRBO
Perfect weekend getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Five Star quality private home in the historic Murray Hill neighborhood of Annapolis, around the corner from the town ce ...
From $1064 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 $345 per night (USD)VRBO
Charming cottage with parking. Easy walk to downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street withi ...
From $345 per night (USD)VRBO
From $1438 per night (USD)VRBO
Beautiful home w\/elevator going to every floor. This house is accessible to all.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $1438 per night (USD)VRBO
From $518 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 $518 per night (USD)VRBO
From $1256 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 $1256 per night (USD)VRBO
From $685 per night (USD)VRBO
Coastal Cottage - 3 BR -Retreat Near Annapolis | Bay Views | Beach Access
- 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 $685 per night (USD)VRBO
From $894 per night (USD)Expedia
Elegant yet modern historic home in the heart of downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
STR-143426 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $894 per night (USD)Expedia
From $605 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 $605 per night (USD)VRBO
From $1350 per night (USD)VRBO
Commissioning Week Escape with Pool and Beautiful 4 Seasons room
- 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 $1341 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 $1341 per night (USD)VRBO
From $1233 per night (USD)Expedia
RARELY AVAILABLE FOR COMMISSIONING WEEK! Complete WATERFRONT LIVING!
- 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 $1233 per night (USD)Expedia
From $936 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 $936 per night (USD)VRBO
From $761 per night (USD)Expedia
REDUCED RATES FOR COMMISSIONING WEEK 2025- Location=AMAZING! Garage Parking for 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $761 per night (USD)Expedia
From $904 per night (USD)VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
RENT-005995-2024 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $904 per night (USD)VRBO
From $216 per night (USD)Expedia
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 $216 per night (USD)Expedia
From $514 per night (USD)VRBO
Fully Furnished 4 Bedroom\/3 Bathroom Single Family Home in Annapolis just a few minutes from downtown
- 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 $514 per night (USD)VRBO
From $1834 per night (USD)VRBO
REDUCED RATE FOR COMMISSIONING WEEK - 2025- DOWNTOWN WATERFRONT HOME
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
NBS23-145368 - This exclusive waterfront property is a rare gem, available for rent only two weeks each year, making it ...
From $1834 per night (USD)VRBO
From $1557 per night (USD)VRBO
4 BR on a Quiet Downtown Annapolis Street: Perfect Blend of Yesteryear Charm and Modern Comforts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
NBS22-145097 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1557 per night (USD)VRBO
From $1065 per night (USD)Expedia
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
- 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 $1065 per night (USD)Expedia