Annapolis Rentals
From $443 per night (USD)VRBO
Newly Updated EV Charger Ready Peaceful Home in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our stylish and modern home, where comfort meets convenience! Here's what you can expect during your stay: ✔ ...
From $443 per night (USD)VRBO
From $201 per night (USD)VRBO
Governor Calvert King, Historic Inns, Four-Poster Bed, Dining, Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $201 per night (USD)VRBO
From $492 per night (USD)VRBO
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Still available for Commissioning Week 2025! This beautifully-restored 1 bedroom apartment is on the lower level of a 2 ...
From $492 per night (USD)VRBO
From $1378 per night (USD)Expedia
Eastport Classic Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to our Eastport home where hardwood floors, large windows that allow ample natural light, and a cozy fi ...
From $1378 per night (USD)Expedia
From $550 per night (USD)VRBO
Ahoy! The Buccaneer with 3-Seasons Room, Private Fenced-In Yard and Game Room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Still available for Commissioning Week 2025! Welcome to The Buccaneer, a family-friendly home located just 3 miles from ...
From $550 per night (USD)VRBO
From $1107 per night (USD)VRBO
Stunning remodel in Murray Hill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We just completed renovations on this spacious h ...
From $1107 per night (USD)VRBO
From $290 per night (USD)VRBO
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this delightful three-bedroom getaway nestled within the ancient Annapolis historical area! Nestled just a 17-m ...
From $290 per night (USD)VRBO
From $717 per night (USD)Expedia
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis/Eastport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Annapolis at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 full bed, this tremendous pro ...
From $717 per night (USD)Expedia
From $478 per night (USD)VRBO
Five Star Charmer! Great Location Downtown & Stadium! Parking too!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
New to the market and just in time for Navy Football. Located at the five star Corner House. Conveniently located on th ...
From $478 per night (USD)VRBO
From $969 per night (USD)Expedia
Perfect Townhouse for USNA Commissioning Week!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to the perfect townhouse for USNA Commissioning Week! As a former midshipman, I know how important it is to have ...
From $969 per night (USD)Expedia
From $336 per night (USD)VRBO
Naval Academy Gate 1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommod ...
From $336 per night (USD)VRBO
From $536 per night (USD)VRBO
Charming on Charles
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our elegant stand alone charming home on Charles Street in Historic Annapolis . This 3 bedroom 2.5 bath is ju ...
From $536 per night (USD)VRBO
From $832 per night (USD)VRBO
New! All Star Annapolis Retreat - Walk to Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to our Town- House in Annapolis Maryland. This charming 1.5-story retreat offers 2,400 square feet of t ...
From $832 per night (USD)VRBO
From $546 per night (USD)Expedia
Newly renovated in DTA w parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom, 2.5-bath single-family home mixes modern renovations with 1896 classic charm. It's been decorated with u ...
From $546 per night (USD)Expedia
From $495 per night (USD)VRBO
Walking distance to Navy Stadium! No cleaning fees!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This centrally located 3-story rental is steps away from everything Annapolis offers! Whether you're in town to explore ...
From $495 per night (USD)VRBO
From $381 per night (USD)Expedia
Cozy apartment in Historic Annapolis with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Annapolis apartment is located within walking distance of everything Annapolis has to offer. Located just outside ...
From $381 per night (USD)Expedia
From $362 per night (USD)VRBO
Newly Renovated Downtown Annapolis Charm - Game Room, Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Home in the Historic District! You will be in the heart of downtown Annapolis. Walk to USNA, St. John's College, the St ...
From $362 per night (USD)VRBO
From $988 per night (USD)Expedia
Naptown Villa House S
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Welcome to the Naptown Villa house! This fully-renovated home located in downtown Annapolis has all the thought ...
From $988 per night (USD)Expedia
From $736 per night (USD)VRBO
Admiral's Abode Abode
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 4-bedroom, 3-bath home in the heart of downtown Annapolis! This beautifully updated property is steps from the ...
From $736 per night (USD)VRBO
From $592 per night (USD)Expedia
Elegant & Bright Historic Home 3BR\/2,5BA, 2 kings, 1 queen, 5 min to USNA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek ...
From $592 per night (USD)Expedia
From $683 per night (USD)VRBO
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 15
Summary: This charming 5 BR (3x true bedrooms and 2x basement rooms with bunk beds) home is conveniently located in Anna ...
From $683 per night (USD)VRBO
From $611 per night (USD)Expedia
Charming Historic Row House in The Heart of Eastport's Horn Point
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this stunning historic rowhouse located in the charming and highly sought-after neighborhood of Horn Point Ea ...
From $611 per night (USD)Expedia
From $1112 per night (USD)VRBO
Available for Commissioning Week and Boat shows. Heated Pool and great backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay comfortably in my home in Annapolis at this 3-bedroom house. With a king bed, queen bed, and two cozy sofa beds, t ...
From $1112 per night (USD)VRBO
From $555 per night (USD)Expedia
New Eastport home with parking, dog-friendly & steps to shops with backyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
New listing available for Commissioning Week 2025! Charming 1905 Eastport Duplex: Historic Character Meets Modern Comfo ...
From $555 per night (USD)Expedia
From $417 per night (USD)VRBO
Timeless Charm Meets Modern Comfort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 3-bedroom, 2.5 bath historic duplex in downtown Annapolis offers a perfect blend of timeless character and ...
From $417 per night (USD)VRBO
From $1199 per night (USD)Expedia
New luxury home in Downtown Annapolis with parking & multiple outdoor spaces
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this beautifully remodeled, professionally designed home in the family-friendly Murray Hill neighborhood of A ...
From $1199 per night (USD)Expedia
From $431 per night (USD)VRBO
Annapolis Blue and Gold Haven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Nestled in the heart of Annapolis, this charming 2-bedroom townhome offers the perfect blend of comfort and con ...
From $431 per night (USD)VRBO
From $316 per night (USD)Expedia
Cozy 2-bedroom home with WiFi and huge backyard minutes from downtown Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Annapolis, this delightful house is a dream. With 2 cozy bedrooms, heating, AC, WiFi, and a washing machine, ...
From $316 per night (USD)Expedia
From $361 per night (USD)VRBO
Charming apt in the heart of Eastport & Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Start your Annapolis adventure in this charming 1-bedroom apartment, comfortably accommodating up to 7 guests. Located i ...
From $361 per night (USD)VRBO
From $345 per night (USD)VRBO
Robert Johnson Queen at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $345 per night (USD)VRBO
From $310 per night (USD)VRBO
Explore Local Attractions, Just Across Maryland State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $310 per night (USD)VRBO
From $831 per night (USD)VRBO
Robert Johnson Suite at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $831 per night (USD)VRBO
From $602 per night (USD)VRBO
Experience History in Annapolis, Near Chesapeake Bay & Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $602 per night (USD)VRBO
From $350 per night (USD)VRBO
Worry-free Stay, Allergy-friendly Room, Exceeds HEPA Standards
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $350 per night (USD)VRBO
From $342 per night (USD)VRBO
Robert Johnson 2 Double Beds Pure Wellness Room at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $342 per night (USD)VRBO
From $381 per night (USD)VRBO
Robert Johnson 1 King Bed Pure Wellness Room at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $381 per night (USD)VRBO
From $304 per night (USD)VRBO
Robert Johnson 1 Queen Bed Pure Wellness Room at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $304 per night (USD)VRBO
From $343 per night (USD)VRBO
Prime Location! Close to Chesapeake Bay & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $343 per night (USD)VRBO
From $363 per night (USD)VRBO
Allergy-friendly Unit, Short Drive to Annapolis Westfield Mall
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $363 per night (USD)VRBO
From $445 per night (USD)VRBO
Surrounded with History! Pet-friendly Accommodation
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $445 per night (USD)VRBO
From $689 per night (USD)VRBO
Pet-friendly Accommodation at Historic Inns of Annapolis! Enjoy Historic Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $689 per night (USD)VRBO
From $290 per night (USD)VRBO
Maryland Inn Queen at Historic Inns of Annapolis, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $290 per night (USD)VRBO
From $856 per night (USD)VRBO
Maryland Inn Suite at Historic Inns of Annapolis, Pet-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $856 per night (USD)VRBO
From $440 per night (USD)VRBO
Top Location! Accommodation Close to Annapolis Historic Sites!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $440 per night (USD)VRBO
From $341 per night (USD)VRBO
Governor Calvert King Balcony at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $341 per night (USD)VRBO
From $586 per night (USD)VRBO
Governor Calvert Suite at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $586 per night (USD)VRBO
From $499 per night (USD)VRBO
Right Where History Is! Just Across Maryland State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $499 per night (USD)VRBO
From $377 per night (USD)VRBO
Governor Calvert Historic King at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $377 per night (USD)VRBO
From $641 per night (USD)VRBO
Historic Architecture In and Out, Memorable Stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $641 per night (USD)VRBO
From $691 per night (USD)Expedia
Charming Annapolis Townhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Historic Annapolis Living! Welcome to your captivating 2-bedroom, 1.5-bath home. This stunning retreat offers a ...
From $691 per night (USD)Expedia
From $491 per night (USD)VRBO
Modern condo in the heart of DTA with garage parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the heart of downtown Annapolis in this bright, modern 2 bed, 2 bath condo with your own private balcony—just st ...
From $491 per night (USD)VRBO
From $387 per night (USD)VRBO
Annapolis Academy Holiday Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our Academy Holiday Home, where we invite you to visit, relax, and spend time with family and friends (and yo ...
From $387 per night (USD)VRBO
From $580 per night (USD)VRBO
Charming Annapolis Retreat with Hidden Wine Room
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Discover charm in our 2BR, 1BA Eastport home, just a stroll away from downtown Eastport (under 1 mile), Downtow ...
From $580 per night (USD)VRBO
From $343 per night (USD)VRBO
Historic Downtown Annapolis Gem
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Experience historic charm with modern upgrades in this 2-bed, 2.5-bath home in the heart of Downtown Annapolis. ...
From $343 per night (USD)VRBO
From $828 per night (USD)VRBO
Pet-Friendly Home Near USNA Stadium with Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Discover the charm of West Annapolis in our 4 bed, 2 bath home. Just steps away from dining, shops, and the new ...
From $828 per night (USD)VRBO
From $268 per night (USD)Expedia
Charming Rental in the Heart of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Charming studio guest house in the heart of Eastport, just half a mile from downtown Annapolis and steps away f ...
From $268 per night (USD)Expedia
From $463 per night (USD)VRBO
Charming Annapolis Waterfront Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Discover the charm of CAPTAINS QUARTERS, your exclusive waterfront retreat in the prestigious Yacht Club Condom ...
From $463 per night (USD)VRBO
From $359 per night (USD)VRBO
Charming Annapolis Home with Cozy Outdoor Hangout
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Freshly renovated 2BR/2BA home in Eastport, Annapolis. Sleeps 6 with brand-new furniture. Enjoy the spacious fe ...
From $359 per night (USD)VRBO
From $233 per night (USD)VRBO
\"The Studio\" Apartment in Colonial Historic District, Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...
From $233 per night (USD)VRBO
From $367 per night (USD)VRBO
\"The Flat\" Apartment in Colonial Historic District, Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...
From $367 per night (USD)VRBO
From $380 per night (USD)VRBO
The Penthouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, The Condu ...
From $380 per night (USD)VRBO
From $484 per night (USD)VRBO
Boat-N-Breakfast! Luxurious Accommodations Aboard a 44' Catamaran
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The most fun way to visit America's Sailing Capital, on the water accommodations aboard the sailcat Zep Tepi! Our cata ...
From $484 per night (USD)VRBO
From $305 per night (USD)VRBO
Charming 2-bedroom apartment with WiFi, AC, kitchen, wash/dryer in Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Unwind in Annapolis at this charming 2 bedroom apartment. Master bedroom includes a queen bed and second smaller fits a ...
From $305 per night (USD)VRBO
From $114 per night (USD)VRBO
Waterfront condo in Eastport, ONLY available for the Legislative session
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
On Back Creek in Eastport, this delightful condo offers 2 bedrooms - one with a king bed and the other with a cozy murph ...
From $114 per night (USD)VRBO
From $604 per night (USD)VRBO
Charming 4-bedroom house 2 blocks from the Navel Academy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 4-bedroom house in Annapolis is perfect for your escape to relaxation. With 4 queen beds and 3 bathrooms equipped w ...
From $604 per night (USD)VRBO
From $484 per night (USD)Expedia
Spacious home in historic Annapolis, near USNA
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Annapolis, enjoy what this 3-bedroom house has to offer. With 2 queen beds and 2 twin bed, guests can relax i ...
From $484 per night (USD)Expedia
From $1375 per night (USD)VRBO
Upscale home in Eastport / Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Ideal location in the heart of Eastport, walking distance to everything Annapolis offers. Only 3 blocks to the Spa Creek ...
From $1375 per night (USD)VRBO
From $497 per night (USD)Expedia
Chesapeake Comfort, Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Bungalow Home that is professionally cleaned and is a full time short-term rental. I have been a Superhost wit ...
From $497 per night (USD)Expedia
From $1077 per night (USD)VRBO
Historic Annapolis With Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Historic home with off-street parking for three cars and three blocks from the USNA. Across the Street from St. John Co ...
From $1077 per night (USD)VRBO
Click For PricingExpedia
Charming Annapolis home in Eastport, Now available Commissioning Week!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This delightful restored home is just 3 blocks away from the Eastport Bridge and 1.3 miles away from the Naval Academy ...
Click For PricingExpedia
From $638 per night (USD)VRBO
Private yard and screened porch at Historic happy home, steps to Main Street with parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...
From $638 per night (USD)VRBO
From $1102 per night (USD)Expedia
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
A perfect harmony of classic and modern, this newly renovated property has a quintessential Annapolis feel. Nestled in t ...
From $1102 per night (USD)Expedia
From $247 per night (USD)VRBO
Cozy Bungalow w/ Ample Outdoor Space Near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to my charming Annapolis home in Eastport! My cozy 1 bed/1 bath house features a versatile spare room perfect fo ...
From $247 per night (USD)VRBO
Click For PricingExpedia
Charming Historic Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful historic home is situated directly across the street from the Paca House, and only three blocks from the ...
Click For PricingExpedia
From $317 per night (USD)VRBO
Cheerful 3-Bedroom House in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Private 3 floor house located at the edge of Annapolis historic district. You can be certain that you will have all the ...
From $317 per night (USD)VRBO
From $335 per night (USD)VRBO
Perfect Eastport Location, walk everywhere, Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Leave your car behind and walk to everything Annapolis, Eastport is full of charm, Restaurants, Museums, live music. Com ...
From $335 per night (USD)VRBO
From $928 per night (USD)VRBO
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Be ...
From $928 per night (USD)VRBO
From $615 per night (USD)VRBO
3 bdrm close to city center, great yard & parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Approx .7 mile to stadium, 1.4 to Naval Academy. Walk to free shuttle at Park Place and to great coffee every morning fr ...
From $615 per night (USD)VRBO
From $954 per night (USD)VRBO
Annapolis 4 BR w/ Gameroom & fire pits-walk everywhere!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This is the perfect house for your family friendly visit to Annapolis, MD Enjoy everything the sought after Eastport ne ...
From $954 per night (USD)VRBO
From $634 per night (USD)Expedia
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a beautiful house for your stay in Annapolis! This large fully renovated house is just off West Street, 1.5 mil ...
From $634 per night (USD)Expedia
From $824 per night (USD)VRBO
Luxe Houseboat: Breathtaking Skyline 360 Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
| OVERVIEW | Welcome to FLOHOM 1 | Bay Escape, your home away from shore! Our luxury houseboat is docked at the premie ...
From $824 per night (USD)VRBO
From $824 per night (USD)Expedia
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this mid-century modern, Cape Cod in West Annapolis. This "Ralph-Lauren Cottage" exudes that "Annapolitan fee ...
From $824 per night (USD)Expedia
From $340 per night (USD)VRBO
Belle By The Bay Summ
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This lovely home has 3 bedrooms, 2.5 bathrooms, fully equipped kitchen with large island that seats 4 and an ou ...
From $340 per night (USD)VRBO
From $269 per night (USD)Expedia
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 $269 per night (USD)Expedia
From $489 per night (USD)VRBO
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 $489 per night (USD)VRBO
From $357 per night (USD)VRBO
Modern studio apartment 5 minute walk to downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Modern efficiency apartment with king bed, seating area with 2 recliner chairs for watching TV. Set up for remote work ...
From $357 per night (USD)VRBO
From $1220 per night (USD)VRBO
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The location is ideal - one short block to USNA Gate 3, and just 4 blocks to the downtown waterfront. Home has a privat ...
From $1220 per night (USD)VRBO
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Hideaway in the middle of everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Clean, spacious Eastport cottage in a prime location to downtown Annapolis and the United States Naval Academy. Both are ...
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From $626 per night (USD)VRBO
Free Parking at Townhome 1 Block to Capital Bldg with Multiple Gathering Spaces & Private Backyard
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Naptown Nook, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in th ...
From $626 per night (USD)VRBO
From $846 per night (USD)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 ...
From $846 per night (USD)Expedia
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USNA Commissioning Week 2023 Downtown Annapolis House that sleeps 13 people
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This 3 story half duplex is in the perfect location, situated in historical downtown Annapolis with a modern day feel, r ...
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From $285 per night (USD)Expedia
Cozy Home in Beautiful Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Keep it simple at this peaceful and centrally located Annapolis home. It has all the amenities and essentials of a home ...
From $285 per night (USD)Expedia
From $414 per night (USD)VRBO
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Little House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $414 per night (USD)VRBO
From $909 per night (USD)Expedia
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Harrison Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $909 per night (USD)Expedia
From $1533 per night (USD)VRBO
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1533 per night (USD)VRBO
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Beautifully Furnished Home, Steps to USNA Stadium, Walk to Downtown Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 BR/3 Bath home is literally steps from the USNA Stadium (graduation) and within walking distance of downtown Anna ...
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From $422 per night (USD)VRBO
Luxury Gourmet Kitchen with Backyard and Parking at 1st floor Eastport Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Still available for Commissioning Week 2025! This beautifully upgraded one-bedroom apartment on the 1st floor of a two- ...
From $422 per night (USD)VRBO
From $174 per night (USD)VRBO
2 BR home on quiet street in Eastport with lovely screened porch.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
RENT-004550-2024 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE B ...
From $174 per night (USD)VRBO
From $264 per night (USD)VRBO
Summer Special in Annapolis! Pristine, Peaceful, Walkable 1B/1B Apt. Sleeps 4.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Fox Haven, a bright, pristine 1 Bed/1 Bath apartment that sleeps 3-4 adults comfortably and has its own separ ...
From $264 per night (USD)VRBO
From $1588 per night (USD)Expedia
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
The Oaks Inn is an exceptional well-kept home, nestled in the heart of Historic Downtown Annapolis, that seamlessly comb ...
From $1588 per night (USD)Expedia