Severn River Rentals
- From $924 per night (USD)
VRBO
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Waterside with it All Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $924 per night (USD)VRBO
- From $891 per night (USD)
Expedia
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Anchors Aweigh Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $891 per night (USD)Expedia
- Click For Pricing
VRBO
Modern home with a fenced yard, W\/D, AC & high-end appliances - walk town
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Stadium Splendour Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingVRBO
- From $609 per night (USD)
Expedia
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W\/D
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The Ship's Bridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $609 per night (USD)Expedia
- Click For Pricing
Expedia
Upscale & updated multi-level home with private courtyard, grill & gas fireplace
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The Pacific Fleet House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For PricingExpedia
- From $1318 per night (USD)
Expedia
Renovated historic home with courtyard, balcony, grill, great downtown location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Submariners Gate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $1318 per night (USD)Expedia
- Click For Pricing
VRBO
Beach House (Annapolis) Bay Ridge Community
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Relax on the front porch while enjoying sweeping views of the Chesapeake Bay. Enjoy the beach right in front of house. P ...
Click For PricingVRBO
- From $614 per night (USD)
Expedia
Waterfront Jolly Roger with Private Pier mins to Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is o ...
From $614 per night (USD)Expedia
- From $230 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 $230 per night (USD)VRBO
- From $703 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 $703 per night (USD)VRBO
- From $240 per night (USD)
VRBO
Charming English Cottage in the heart of Eastport - park the car and walk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Restored and charming 2 bedroom 1.5 bath historic (circa 1921) cottage located in the heart of the popular Eastport and ...
From $240 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $295 per night (USD)Expedia
- From $444 per night (USD)
VRBO
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This fully renovated three bedroom home sleeps 8. A touch of Key West comes to Eastport in this beautiful cottage style ...
From $444 per night (USD)VRBO
- From $584 per night (USD)
Expedia
1 Block to USNA with Chapel Views big back patio and off-site parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $584 per night (USD)Expedia
- From $279 per night (USD)
VRBO
Private Annapolis Guest Apartment! Walkable to downtown! Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Keep it simple at this peaceful and centrally located guesthouse. This charming guest house w/ private access is located ...
From $279 per night (USD)VRBO
- From $285 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 $285 per night (USD)VRBO
- From $935 per night (USD)
VRBO
The Cottage on Back Creek
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
STR22-145133 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE A ...
From $935 per night (USD)VRBO
- From $525 per night (USD)
Expedia
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $525 per night (USD)Expedia
- From $340 per night (USD)
VRBO
New listing …. Beautiful Home close to it all.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
This cozy yet spacious home offers 3 queen beds, a twin over full bunk bed with a pull out trundle, 2 full baths, 2 kitc ...
From $340 per night (USD)VRBO
- From $174 per night (USD)
VRBO
Ideal Eastport\/ Annapolis Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This spacious, fully furnished one bedroom1st floor apartment is perfectly located and has everything you need for your ...
From $174 per night (USD)VRBO
- Click For Pricing
VRBO
Downtown furnished apartment - walking distance to restaurants
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Church owned 2nd Floor apartment in historic house - fully furnished - eat-in kitchen, dining room and living room - has ...
Click For PricingVRBO
- From $424 per night (USD)
Expedia
Stay just steps from the Waterfront in the modern Historic Fleet's Inn
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Stay just steps from the Annapolis waterfront! Cherished by the multi-generational Navy owners who have updated the mod ...
From $424 per night (USD)Expedia
- From $564 per night (USD)
VRBO
Hanover House across from USNA Gate 3 with private back patio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $564 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Bay View Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $250 per night (USD)Expedia
- From $413 per night (USD)
VRBO
Blue & Gold House: Walk to Navy Stadium w\/ parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Blue & Gold House, across the street from the Navy Stadium & a short walk to shopping & dining in Downtow ...
From $413 per night (USD)VRBO
- From $661 per night (USD)
Expedia
Quiet home with large yard, close to Navy Bridge.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come relax at our spacious home and enjoy our quiet neighborhood! We are located near the greatest attractions in Annapo ...
From $661 per night (USD)Expedia
- From $910 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 $910 per night (USD)VRBO
- Click For Pricing
Expedia
Easy Annapolis lodging - still available for Sailboat Show!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This home (divided/upper floor only) is perfect for families, situated on a quiet residential street with a gorgeous bac ...
Click For PricingExpedia
- From $323 per night (USD)
VRBO
ACROSS FROM STADIUM - walk to downtown Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $323 per night (USD)VRBO
- From $506 per night (USD)
Expedia
Great location, free parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
‘Perfect location’ (Ernesto) ‘Loved the house!! Amazing!’ (Aaron) “So much attention to detail.” (Juniper) “Never staye ...
From $506 per night (USD)Expedia
- Click For Pricing
Expedia
Hidden Gem Downtown! Walk to USNA!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
You will be located in the heart of downtown Annapolis! Located right next to the Maryland Inn and steps away from shops ...
Click For PricingExpedia
- From $325 per night (USD)
VRBO
Gem in Downtown Annapolis, close to USNA, St. John's College
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryla ...
From $325 per night (USD)VRBO
- From $661 per night (USD)
VRBO
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 $661 per night (USD)VRBO
- From $809 per night (USD)
Expedia
Steps to Gate 1 and Free Parking at Naval-Academy Themed Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to this gorgeous 1900's fully-renovated home, restored to a new modern grandeur, which includes coveted parking ...
From $809 per night (USD)Expedia
- From $558 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
421 Irie City Of Annapolis License Number 145052 Please note 2026 and beyond commissioning week will need to be confirm ...
From $558 per night (USD)VRBO
- From $380 per night (USD)
Expedia
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfec ...
From $380 per night (USD)Expedia
- From $308 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 $308 per night (USD)VRBO
- From $802 per night (USD)
Expedia
Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Base Camp on the Lake Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $802 per night (USD)Expedia
- From $1028 per night (USD)
VRBO
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The Morning Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1028 per night (USD)VRBO
- From $1585 per night (USD)
Expedia
Lakefront home with private pool, hot tub, outdoor space, central AC, & W\/D
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1585 per night (USD)Expedia
- From $1161 per night (USD)
VRBO
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1161 per night (USD)VRBO
- Click For Pricing
VRBO
Luxe Waterfront Yacht: Pool\/Kayak\/SUP\/Tube on Bay, Owner's Suite, Mins from town
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
GENERAL DESCRIPTION Welcome to our wonderful 5BR/5BTH home SERENDIPITY, an 83-ft superyacht sailboat docked in Back Cree ...
Click For PricingVRBO
- From $400 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 $400 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Historic Annapolis Home And Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This delightful two bedroom, two full bath duplex occupies the second and third floors of a lovely home built in 1900, u ...
From $350 per night (USD)VRBO
- From $383 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment in Historic Downtown Annapolis steps away from the main entrance of the Naval Academy. Upstairs ...
From $383 per night (USD)VRBO
- From $662 per night (USD)
VRBO
Waterfront Oasis in Eastport - Walk to Downtown and USNA
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our newest listing in listing in the Maritime section of Annapolis . This upscale , fully renovated waterfron ...
From $662 per night (USD)VRBO
- From $383 per night (USD)
VRBO
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 $383 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $695 per night (USD)
VRBO
Heart of Downtown, superior location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Steps from the Annapolis City Dock and U.S. Naval Academy- Walk to all Shops, Restaurants, and Downtown Events. This pr ...
From $695 per night (USD)VRBO
- From $450 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 $450 per night (USD)VRBO
- From $189 per night (USD)
VRBO
Beautiful Condo - Water View Near City Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Newport Condominium has a beautiful water view of Spa Creek in Eastport. This condo is newly decorated with new ca ...
From $189 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Jackson's Bunker in Eastport with fenced-in backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the Annapolis "Republic of Eastport", this charming pet-friendly home is a short walk to restaurants, shops, ...
From $292 per night (USD)Expedia
- From $650 per night (USD)
VRBO
Charming 235-yo former tavern 1 block to water\/shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
235 yo home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with antiques ...
From $650 per night (USD)VRBO
- From $210 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 $210 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Eastport Gem - Popular house walk to Downtown & USNA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*Flexible Commissioning Week Cancellation Policy* This unique 3 Bedroom/3 Bath home is located in Eastport - next door ...
From $500 per night (USD)VRBO
- From $1150 per night (USD)
VRBO
Gatehouse Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy the beauty and convenience of Historic Downtown Annapolis and the U.S. Naval Academy. This 5 BR/ 4.5 baths home of ...
From $1150 per night (USD)VRBO
- From $444 per night (USD)
VRBO
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
- Bedrooms:
- 4
- 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 $444 per night (USD)VRBO
- From $561 per night (USD)
Expedia
Stay in USNA-themed dog-friendly home steps from Navy Stadium
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
In Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the ...
From $561 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $160 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 $160 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Quiet Neighborhood 2.3 miles from Downtown w\/FREE parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Spinnakers Run, nestled just 2.3 miles from Historic Downtown Annapolis and Eastport with plenty of free park ...
From $375 per night (USD)VRBO
- From $344 per night (USD)
Expedia
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 $344 per night (USD)Expedia
- From $829 per night (USD)
VRBO
High-end Eastport home with private pool, hot tub, grill & off-street parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Third Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $829 per night (USD)VRBO
- Click For Pricing
VRBO
Historic Downtown Luxury. Your own oasis but close to everything with parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
PLEASE NOTE: We are only renting this house for commissioning week. The McCusker house has historical charm with high-e ...
Click For PricingVRBO
- From $161 per night (USD)
VRBO
Freshly renovated 3-story home 1 block from USNA!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to The Wardroom! Originally built in 1902 and completely renovated in 2014, this 3 story home is the p ...
From $161 per night (USD)VRBO
- From $919 per night (USD)
Expedia
All newly renovated and ready for new guests at Eastport Retreat - private back patio with parking
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
*Flexible Commissioning Week Cancellation Policy* This unique home was originally built in 1927, and has been fully res ...
From $919 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $413 per night (USD)
Expedia
Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Naptown Nook, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in th ...
From $413 per night (USD)Expedia
- From $638 per night (USD)
VRBO
MODERN 2022 NEWLY BUILT TOWNHOME
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...
From $638 per night (USD)VRBO
- From $1548 per night (USD)
Expedia
Picturesque home with yard, central AC, washer\/dryer & cable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Stadium Gardens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $1548 per night (USD)Expedia
- From $450 per night (USD)
VRBO
7 mins away from Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
Come stay at our cozy house. Perfect for a group of 11people. Share beautiful memories that will last a lifetime. Close ...
From $450 per night (USD)VRBO
- Click For Pricing
Expedia
Lovely 1 bedroom rental in downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Keep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to offer! The ...
Click For PricingExpedia
- Click For Pricing
VRBO
Adorable 1 bedroom apartment in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a stylish experience at this centrally-located apartment. 2 minute walk to Main Street and all of the attractions ...
Click For PricingVRBO
- From $388 per night (USD)
VRBO
Escape Villa in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $388 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Darling 2 BR home with parking in the sought after Murray Hill section of Historic Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STR22-145187 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $500 per night (USD)VRBO
- From $401 per night (USD)
Expedia
Serene, riverfront home with deck, balcony, kitchen & fireplace - dog-friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Severn View of Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $401 per night (USD)Expedia
- From $310 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 $310 per night (USD)VRBO
- From $979 per night (USD)
Expedia
Stunning, Large Historic Annapolis Home, Steps to Academy and Downtown.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
**Under New Ownership** Experienced owner with multiple properties. Owners live locally, property manager resides in Cit ...
From $979 per night (USD)Expedia
- Click For Pricing
VRBO
NEW lovely studio apartment with onsite parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located place! (Two guests maximum) The space null. Other things to note Pl ...
Click For PricingVRBO
- Click For Pricing
Expedia
Charming Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastp ...
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- Click For Pricing
Expedia
Condo Houseboat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This BRAND NEW condo house boat is nestled in Back Creek. The views of the Chesapeake Bay are amazing! This is the best ...
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- From $422 per night (USD)
VRBO
Chesapeake Comfort, Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Bungalow Home that is professionally cleaned and is a full time Airbnb. I have been a Superhost with other lis ...
From $422 per night (USD)VRBO
- From $1052 per night (USD)
VRBO
Newly renovated townhome with a fenced yard, gas grill, washer\/dryer, central AC
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Herons Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $1052 per night (USD)VRBO
- From $2758 per night (USD)
Expedia
Riverfront home with dock, private outdoor pool, gas grill, deck & great views
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 9
Weems Shelby Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $2758 per night (USD)Expedia
- From $582 per night (USD)
VRBO
Lovely home with a deck, gas grill, AC, firepit, & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Portside Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $582 per night (USD)VRBO
- From $1074 per night (USD)
Expedia
Upscale multi-level retro home with large deck, washer\/dryer, and lovely patio
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
St Johns Adjacent Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1074 per night (USD)Expedia
- From $1370 per night (USD)
VRBO
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Ensign's Ridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1370 per night (USD)VRBO
- From $855 per night (USD)
Expedia
Huge deck overlooking water
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Renovated, charming Annapolis home on half-acre lot fronting Burley Creek. Just a short paddle to Whitehall Bay and expa ...
From $855 per night (USD)Expedia
- From $265 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 $265 per night (USD)VRBO
- From $1400 per night (USD)
VRBO
Reno'd Home in West Annapolis: Great for Stadium Events, Boat Shows & Downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
West Annapolis is a neighborhood close to everything, but with peace and quiet in mind. Shopping and food options are c ...
From $1400 per night (USD)VRBO
- From $787 per night (USD)
VRBO
Annapolis 4 BR House w\/ Cottage and Gameroom
- Bedrooms:
- 4
- 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 $787 per night (USD)VRBO
- From $390 per night (USD)
Expedia
Charming 1926 renovated home in quite neighborhood perfectly situated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought out ...
From $390 per night (USD)Expedia
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VRBO
Waterfront Magic - 10 minutes from downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
A peninsula on the Severn River located in the beautiful neighborhood of Linstead. This home is a waterfront playground ...
Click For PricingVRBO
- From $120 per night (USD)
VRBO
My Annapolis Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FOUR WEEK MINIMUM STAY beginning July 1st. This fully furnished studio apartment has everything you'll need for a quiet ...
From $120 per night (USD)VRBO
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VRBO
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 PricingVRBO
- From $1765 per night (USD)
VRBO
7BR\/ 5.5 Bath Home AVAILABLE CW 2024, 2025
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
USNA Commissioning Week Rentals welcome! Perfect location for easy access to USNA events! A convenient 5 min drive from ...
From $1765 per night (USD)VRBO
- From $809 per night (USD)
VRBO
Annapolis Villa Aquamarine
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Annapolis and its very own Villa Aquamarine: your exclusive oasis awaits in this exceptional five bedroom hom ...
From $809 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Waterfront 2BR Guest House on Cypress Creek - Severna Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
STR00626 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $350 per night (USD)VRBO
- From $455 per night (USD)
VRBO
Coastal Cabins.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home awa ...
From $455 per night (USD)VRBO
- From $1077 per night (USD)
Expedia
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Annapolis Bay Ridge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $1077 per night (USD)Expedia