Annapolis Rentals
From $566 per night (USD)VRBO
Restriction Retreat - Relax & walk to Main St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $566 per night (USD)VRBO
From $1136 per night (USD)VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 3
- 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 $1136 per night (USD)VRBO
From $417 per night (USD)VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $417 per night (USD)VRBO
From $574 per night (USD)VRBO
Stunning Waterfront Cottage in the Sailing Capital of the World!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience an exceptional waterfront setting in the Sailing Capital of the World. This upgraded 2‑bedroom, 1‑bath cottag ...
From $574 per night (USD)VRBO
From $638 per night (USD)VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment with additional family room with brand new queen sleeper sofa in Historic Downtown Annapolis step ...
From $638 per night (USD)VRBO
From $668 per night (USD)VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. We feature a main level open floor plan ...
From $668 per night (USD)VRBO
Click For PricingVRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
Click For PricingVRBO
From $596 per night (USD)VRBO
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Brid ...
From $596 per night (USD)VRBO
From $465 per night (USD)VRBO
Recently Renovated Annapolis Home - Conveniently Located
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walk ...
From $465 per night (USD)VRBO
From $255 per night (USD)VRBO
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic ...
From $255 per night (USD)VRBO
From $352 per night (USD)VRBO
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This spacious, well-appointed 1 bedroom, 1 European style bath 2nd floor apartment is in the heart of Eastport. You’ll b ...
From $352 per night (USD)VRBO
From $371 per night (USD)VRBO
Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Walk to all Annapolis has to offer, once parked you’ll never need a car. Walk to City Dock, marinas, restaurants, pubs ...
From $371 per night (USD)VRBO
From $702 per night (USD)VRBO
All-stop. Rental Midships.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome ste ...
From $702 per night (USD)VRBO
From $578 per night (USD)VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $578 per night (USD)VRBO
From $1352 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 $1352 per night (USD)VRBO
From $395 per night (USD)VRBO
Charming Annapolis Cottage-Steps from Naval Academy & Downtown with parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your perfect Annapolis escape — a beautifully appointed, fully furnished cottage where every detail has been ...
From $395 per night (USD)VRBO
From $800 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 $800 per night (USD)VRBO
From $304 per night (USD)VRBO
Fleet St Retreat in Downtown - Great Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
We welcome you to our renovation on historic Fleet Street. Purchased in 2016 this house was taken down to the studs so e ...
From $304 per night (USD)VRBO
From $428 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 $428 per night (USD)VRBO
From $1012 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 $1012 per night (USD)VRBO
From $2824 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 $2824 per night (USD)VRBO
From $481 per night (USD)VRBO
Perfect spot for a Weekend Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city ga ...
From $481 per night (USD)VRBO
From $553 per night (USD)VRBO
Historic Downtown Charmer, Water Views and Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep ...
From $553 per night (USD)VRBO
From $736 per night (USD)VRBO
Beautifully Renovated Historic District Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $736 per night (USD)VRBO
From $808 per night (USD)VRBO
Charming Historic Annapolis Home With Two Off-street Parking Places!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitche ...
From $808 per night (USD)VRBO
From $748 per night (USD)Expedia
Nautical Feel to This Beautiful Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
From the minute you walk in the door, you will feel the warmth and charm this home offers. Located on the Eastport si ...
From $748 per night (USD)Expedia
From $972 per night (USD)VRBO
102 5-star Reviews located inside the City of Annapolis in Murray Hill.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located on a dead end street, this charming brick colonial with a slate roof sits on a beautiful lot just 1/2 block from ...
From $972 per night (USD)VRBO
From $765 per night (USD)VRBO
Lots free parking, hot tub, outdoor oasis - NOT party house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Walk downtown or to grocery, restaurants, etc. We live in a nice modernly decorated duplex adjacent to Navy Stadium. I ...
From $765 per night (USD)VRBO
From $865 per night (USD)VRBO
Beautiful Waterfront Townhome In Historic Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minu ...
From $865 per night (USD)VRBO
From $600 per night (USD)VRBO
Historic District\"Crab Cakes and Football\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock ...
From $600 per night (USD)VRBO
From $2295 per night (USD)VRBO
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Built in 1875, this delightful house offers total privacy in the heart of downtown Annapolis. Steps from Main St, and t ...
From $2295 per night (USD)VRBO
From $580 per night (USD)VRBO
4-Bedroom Eastport Haven + Walk to Downtown & USNA + Rare Multi-Car Parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your ultimate Annapolis getaway! Tucked into a quiet, private cul-de-sac in desirable Eastport, our home offe ...
From $580 per night (USD)VRBO
From $279 per night (USD)VRBO
Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready an ...
From $279 per night (USD)VRBO
From $1064 per night (USD)Expedia
Charming Annapolis Victorian
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. W ...
From $1064 per night (USD)Expedia
From $439 per night (USD)VRBO
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Vacations are meant to be carefree! Let the chimes from the Naval Academy chapel start your day. Stroll along our famed ...
From $439 per night (USD)VRBO
From $444 per night (USD)VRBO
Charming 1926 Four Bedroom Home w Ample Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought ou ...
From $444 per night (USD)VRBO
From $1038 per night (USD)VRBO
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Unique opportunity to rent an entire triplex Downtown Annapolis! One property with 3 nearly identical side-by-side uni ...
From $1038 per night (USD)VRBO
From $508 per night (USD)Expedia
Prime Eastport Location - Waterfront Condo w Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience the Difference: Professionally Managed by iTrip Annapolis Waterfront Condo with Spa Creek Views, Rooftop Poo ...
From $508 per night (USD)Expedia
From $608 per night (USD)VRBO
Walk to Main St, City Dock, USNA from Historic Catch 22 w Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis This charming 3-BR, 2.5-BA townhome is just a 1/2- ...
From $608 per night (USD)VRBO
From $735 per night (USD)Expedia
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: This is a gorgeous home with in ground *heated* "6 month" pool & "9 month" hot tub - less than a mile walk fro ...
From $735 per night (USD)Expedia
From $442 per night (USD)VRBO
Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
*** WE ARE COMPLIANT WITH THE CITY OF ANNAPOLIS!!! Strict short term rental rules are in place for this area. We are pro ...
From $442 per night (USD)VRBO
From $808 per night (USD)VRBO
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to acco ...
From $808 per night (USD)VRBO
From $580 per night (USD)VRBO
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to The Buccaneer, a family-friendly home l ...
From $580 per night (USD)VRBO
From $596 per night (USD)Expedia
Steps to USNA with Large Private Patio & Free Off-Site Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Stay in this restored historic Annapolis home, loc ...
From $596 per night (USD)Expedia
From $470 per night (USD)VRBO
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Corner House – Quaint and Cozy 2 Bedroom Suite with Parking The Corner House is a hidden gem located in the quaint P ...
From $470 per night (USD)VRBO
From $438 per night (USD)VRBO
Charming on Charles Street
- 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 jus ...
From $438 per night (USD)VRBO
From $459 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 $459 per night (USD)VRBO
From $197 per night (USD)VRBO
Robert Johnson Queen at Historic Inns of Annapolis | 0.1mi State Circle
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $197 per night (USD)VRBO
Explore Local Attractions | Across Maryland State House | 0.2mi to City Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $197 per night (USD)VRBO
From $316 per night (USD)VRBO
Robert Johnson Suite at Historic Inns of Annapolis | Pet-Friendly + Free Shuttle
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $316 per night (USD)VRBO
From $316 per night (USD)VRBO
Robert Johnson Suite | 0.2mi to William Paca House & 0.3mi to USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $316 per night (USD)VRBO
From $223 per night (USD)VRBO
Close to Naval Academy & State House | Robert Johnson 2 Doubles
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $223 per night (USD)VRBO
From $222 per night (USD)VRBO
Robert Johnson 2 Double Beds Pure Wellness Room at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $222 per night (USD)VRBO
From $222 per night (USD)VRBO
Robert Johnson 1 King Bed Pure Wellness Room at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $222 per night (USD)VRBO
From $223 per night (USD)VRBO
Robert Johnson 1 Queen Bed Pure Wellness Room at Historic Inns of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $223 per night (USD)VRBO
From $223 per night (USD)VRBO
Boutique Historic Stay Near USNA & Annapolis City Dock | 1 King Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $223 per night (USD)VRBO
From $189 per night (USD)VRBO
Elegant Historic Flat: Near State House & Naval Academy | Pets Are Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $316 per night (USD)VRBO
Pet-friendly Accommodation at Historic Inns of Annapolis | 0.3 mi to State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $316 per night (USD)VRBO
From $189 per night (USD)VRBO
Maryland Inn Queen at Historic Inns of Annapolis | Pets are Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $189 per night (USD)VRBO
From $313 per night (USD)VRBO
Maryland Inn Suite at Historic Inns of Annapolis | Pets Are Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $313 per night (USD)VRBO
From $252 per night (USD)VRBO
Top Location | Close to Annapolis Historic Sites | Pets Allowed & Free Shuttle
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $252 per night (USD)VRBO
From $261 per night (USD)VRBO
Governor Calvert King Balcony at Historic Inns of Annapolis | Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $261 per night (USD)VRBO
From $316 per night (USD)VRBO
Governor Calvert Suite at Historic Inns | Steps to Maryland State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $316 per night (USD)VRBO
From $316 per night (USD)VRBO
Rare Antique Gem | Steps to State House | 0.3 Mi to Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
From $316 per night (USD)VRBO
From $994 per night (USD)VRBO
Steps from City Dock w Private Fenced-In Backyard at Historic Dog-Friendly Philip Clayton House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the Difference: Professionally Managed by iTrip Annapolis Historic Philip Clayton House – Downtown Annapolis ...
From $994 per night (USD)VRBO
From $584 per night (USD)Expedia
Historic Annapolis Retreat Steps to the Statehouse & City Dock w Parking & Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis In the shade of the Maryland Statehouse, this hist ...
From $584 per night (USD)Expedia
From $560 per night (USD)VRBO
Historic Row Home | Hot Tub - 1 Block from Gate 1!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church a ...
From $560 per night (USD)VRBO
From $579 per night (USD)Expedia
Walk to the stadium! - Lighthouse on Glenwood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your Annapolis retreat! This fully renovated Homewood colonial is ideal for Commissioning Week, Navy games, t ...
From $579 per night (USD)Expedia
From $634 per night (USD)VRBO
Historic Charm Meets Convenience in the Heart of Annapolis with Large Private Yard & Parking
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to The Yard, a rare ½-acre retreat just st ...
From $634 per night (USD)VRBO
From $766 per night (USD)VRBO
Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Perfect home for families traveling to Annapolis! Your family will be close to everything when you stay at this central ...
From $766 per night (USD)VRBO
From $1131 per night (USD)VRBO
5BR, 3 King Beds, Near Downtown & USNA
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Perfectly sized for groups who want space to spread out — not feel crowded. Enjoy a comfortable, well-designed home just ...
From $1131 per night (USD)VRBO
From $578 per night (USD)Expedia
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
- Bedrooms:
- 2
- 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 $578 per night (USD)Expedia
From $479 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 Ann ...
From $479 per night (USD)VRBO
From $475 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 $475 per night (USD)Expedia
From $952 per night (USD)VRBO
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Walk to Navy-Marine Corps Memorial Stadium from this 2,400 sq ft renovated home with a finished 930 sq ft base ...
From $952 per night (USD)VRBO
From $544 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 $544 per night (USD)Expedia
From $559 per night (USD)VRBO
Waterfront Suite with Views of Annapolis from Prime Eastport Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience the Difference: Professionally Managed by iTrip Annapolis Wake up to sparkling water views and the charm of ...
From $559 per night (USD)VRBO
From $550 per night (USD)Expedia
Fabulous 5-bedroom house with AC in charming Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Looking to explore Annapolis and live comfortably on a budget? This cozy square house will be just right for you! The si ...
From $550 per night (USD)Expedia
From $381 per night (USD)VRBO
Hidden Wine Cellar | Eastport Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: There's a secret downstairs - a hidden wine cellar tucked beneath this Eastport home. Upstairs you'll find 2 b ...
From $381 per night (USD)VRBO
From $555 per night (USD)VRBO
Historic Charm | Steps from City Dock and the Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Walk out the door and you're in the center of Annapolis. This updated 2-bedroom downtown home has 2.5 baths, t ...
From $555 per night (USD)VRBO
From $476 per night (USD)VRBO
Walk to DTA & USNA | Pet-Friendly Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Bring the whole crew — dogs included. This 3-bedroom Annapolis home is walkable to Downtown, Navy tailgates, a ...
From $476 per night (USD)VRBO
From $814 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 $814 per night (USD)VRBO
From $662 per night (USD)VRBO
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Watch the sunrise on the private beach at Oh Happy ...
From $662 per night (USD)VRBO
From $651 per night (USD)VRBO
3 bdrm close to city center, great yard & parking! Perfect for cooks and pets!
- 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 $651 per night (USD)VRBO
From $336 per night (USD)VRBO
Annapolis Charm –Bright 3BR in Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this spacious and fully furnished home, designed to be your comfortable home away from home. Spanning three l ...
From $336 per night (USD)VRBO
From $758 per night (USD)VRBO
4BR-Gameroom-Firepit-Gym-Walkable-Sleeps 13
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This is the perfect house for your family friendly visit to Annapolis! *Please no bachelor/bachelorette parties Enjoy ...
From $758 per night (USD)VRBO
From $945 per night (USD)VRBO
Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Naptown Nook, conveniently located in d ...
From $945 per night (USD)VRBO
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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 ...
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From $315 per night (USD)VRBO
Pristine Downtown 1-Bedroom Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minute ...
From $315 per night (USD)VRBO
From $426 per night (USD)Expedia
Historic Downtown House with Off Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park you ...
From $426 per night (USD)Expedia
From $678 per night (USD)VRBO
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 $678 per night (USD)VRBO
From $1215 per night (USD)Expedia
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 $1215 per night (USD)Expedia
From $542 per night (USD)VRBO
Eastport Charmer Summ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Your family will be close to everything when you stay at this charming 2-bedroom cottage nestled in the Eastpo ...
From $542 per night (USD)VRBO
From $511 per night (USD)Expedia
Belle By The Bay Summ
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Escape to Annapolis in this stylish home, perfect for large groups! Enjoy a private brick patio with a fire pi ...
From $511 per night (USD)Expedia
From $855 per night (USD)VRBO
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Discover 'The Crabby Patty,' a spacious 3-BR, 2.5-BA home in the heart of downtown Annapolis. Blending modern ...
From $855 per night (USD)VRBO
From $684 per night (USD)VRBO
Charming Eastport CapeCod
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful Cape Code made for entertaining, this Eastport home is perfect for your next trip to Annapolis! Newly renovate ...
From $684 per night (USD)VRBO
From $1758 per night (USD)VRBO
Spacious Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This lovely 4-bedroom home boasts 3 full bathrooms and room to comfortably sleep up to 12 people. With its spacious and ...
From $1758 per night (USD)VRBO
From $1738 per night (USD)Expedia
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
The Oaks Inn is a well-kept home, built in 1860 with original hardwood floors. It is nestled in the heart of Historic Do ...
From $1738 per night (USD)Expedia
From $365 per night (USD)VRBO
Arts District - Peaceful, Sparkling, 1 Bed/1 Bath, Walk to Navy Stadium and Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Fox Haven, a bright, pristine 1 Bed/1 Bath apartment that sleeps 3 adults comfortably and has its own separat ...
From $365 per night (USD)VRBO
From $514 per night (USD)Expedia
Waterfront 2-Bedroom Condo on Spa Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home in Annapolis! Nestled in the charming neighborhood of Eastport, this beautifully app ...
From $514 per night (USD)Expedia