Anne Arundel Area, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anne Arundel Area, Maryland on RentalSaver.com!

Anne Arundel Area Rentals

$\La Licorne\ Waterfront Beach Cottage$
From $437 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 $437 per night (USD)
VRBO
From $1042 per night (USD)
VRBO
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to The Yellow Annapolis Cottage: A Chesapeake Getaway with Stunning Bay Views Welcome to our Bay Ridge Yellow C ...
From $1042 per night (USD)
VRBO
From $598 per night (USD)
VRBO
Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Experience the Difference: Professionally Managed by iTrip Annapolis A new home but managed by experienced hosts, iTrip ...
From $598 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Heart of Annapolis King George Home Steps to USNA Gate 1 & Main Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Your Historic Annapolis Retreat! Disc ...
From $588 per night (USD)
Expedia
From $696 per night (USD)
VRBO
Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
ALL NEW! Just minutes from USNA Stadium, downtown Annapolis and US Naval Academy, MBA Homes' Nautical Oasis is perfect f ...
From $696 per night (USD)
VRBO
From $58 per night (USD)
VRBO
Efficiency Apartment Close to Annapolis. .
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Furnished efficiency apartment in Annapolis, close to downtown area, and easy access to Highways. Private Entrance, pri ...
From $58 per night (USD)
VRBO
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VRBO
Waterfront Home with Private Dock, Community Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Waterfront Oasis with Private Dock, Firepit & Kaya ...
Click For Pricing
VRBO
From $457 per night (USD)
Expedia
Centrally Located Rancher w/ Parking, Near BWI &
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Your family will be close to everything when you stay at this centrally-located place. 3BD 2BA single level ho ...
From $457 per night (USD)
Expedia
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VRBO
Comfy King Private Suite Near UMD BWMC & BWI with Pool Table and Treadmill.
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Luxury Private Suite Near UMD Hospital & BWI – Comfort, Privacy & Convenience Welcome to your private retreat in a quie ...
Click For Pricing
VRBO
From $1009 per night (USD)
VRBO
Modern Waterfront House with amazing views of the Chesapeake Bay! Private pier!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Experience the perfect blend of modern luxury and coastal charm in this stunning waterfront home on the Chesapeake Bay. ...
From $1009 per night (USD)
VRBO
From $674 per night (USD)
VRBO
Historic Parish House 2-Bedroom Condo Steps to Naval Academy
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step into a truly exceptional condo nestled in a beautifully preserved historic church, just 2 blocks from the U.S. Nava ...
From $674 per night (USD)
VRBO
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Expedia
Premier Retreat: Private Pool, Spa, Fireplace & Spacious Deck
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Spacious Private Getaway – Pool, Spa, Fireplace & Outdoor Entertainment! Welcome to your perfect retreat—a 5-bedroom, 4 ...
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Expedia
From $767 per night (USD)
VRBO
Londontowne Rancher | 3BR | Near Waterfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Easy, one-level living in this 3-bedroom rancher with an en-suite master, full kitchen, and private backyard f ...
From $767 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Cozy Retreat Near Fort Meade | Fire Pit
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our fully furnished, remodeled home just minutes from the MARC station! Perfectly located near Wash ...
From $406 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Peaceful Pet-Friendly Stay - Near USNA and Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax in a bright, open living area designed for comfort and connection. Enjoy: * Plush seating for the whole group * S ...
From $399 per night (USD)
VRBO
From $126 per night (USD)
VRBO
Charming house with WiFi, fitness room, AC in brilliant Severn
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Severn at this fabulous house. With 2 bathrooms and amenities like heating, WiFi, and a fitn ...
From $126 per night (USD)
VRBO
From $488 per night (USD)
VRBO
Annapolis Baystone House
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Our newly updated 4-bedroom, 3.5-bathroom home in Annapolis offers spacious living just 15 minutes from downto ...
From $488 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Annapolis Blue and Gold Haven
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Charming 2-BR Annapolis townhome, perfect for your coastal retreat! Steps from Navy-Marine Corps Memorial Stad ...
From $464 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Studio Apartment in Downtown Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
19th Century Coastal charm with modern comfort! Located in the quiet and beautiful Colonial Historic District, This stud ...
From $213 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Pool & Yard Retreat | 4BR | 20 Min to Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Spread out in this 4-bedroom retreat with a fenced-in pool, large backyard play area, and spacious eat-in kitc ...
From $493 per night (USD)
Expedia
From $1660 per night (USD)
VRBO
18th Century 4bdrm Luxury Historic Home in Downtown Annapolis
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to Lynder's Luxury Lodging-Annapolis. Discover this 4-bedroom Colonial gem in the heart of Downtown Annapolis ( ...
From $1660 per night (USD)
VRBO
From $630 per night (USD)
Expedia
Freshly-Renovated Riverfront Retreat with Private Dock, Deck & Yard for the Whole Family - Dogs Too
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Experience the Difference: Professionally Managed by iTrip Annapolis Escape to this charming riverfront home, just one ...
From $630 per night (USD)
Expedia
From $494 per night (USD)
VRBO
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Water-lovers dream waterfront cottage 15 min to Annapolis, Navy Academy & 40 min from DC with perfect paddleboarding wat ...
From $494 per night (USD)
VRBO
From $865 per night (USD)
VRBO
Zen Sunset Retreat on Waterfront at West River, MD
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
De-stress, Relax and Heal at our stunning, newly-constructed 3-story waterfront Zen Sunset Retreat (ZSR), with tons of a ...
From $865 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 $222 per night (USD)
VRBO
Maryland Inn | Victorian Charm | Queen Room | 0.1mi State House
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 $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 $261 per night (USD)
VRBO
Right Where History Is | Just Across Maryland State House
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 $252 per night (USD)
VRBO
Governor Calvert Historic King at Historic Inns of Annapolis | Pet-Friendly
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 $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 $878 per night (USD)
VRBO
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
Bedrooms:
5
Bathrooms:
6
Sleeps:
18
Summary: Located only 5 miles from Annapolis, this newly updated, 3-story home with great views of the Chesapeake Bay i ...
From $878 per night (USD)
VRBO
From $648 per night (USD)
Expedia
Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience the Difference: Professionally Managed by iTrip Annapolis Available for Commissioning Week 2025! Charmi ...
From $648 per night (USD)
Expedia
From $385 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 $385 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Unique and central in Eastport
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to The Captain's Quarters, a beautifully restored 4BR/3BA home in the heart of walkable, historic Eastport. Old- ...
From $428 per night (USD)
Expedia
From $1380 per night (USD)
VRBO
Spacious 6BR Retreat in Fabulous Severn, Fitness Room, AC & Fast WiFi!
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Welcome to your perfect getaway in fabulous Severn! This spacious 6-bedroom, 4-bathroom home comfortably sleeps 14–16 gu ...
From $1380 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Charming Guest Suite near BWI Airport - Anne Arundel County, MD
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Unwind in this private studio suite, ideal for a couples’ get-away, small group, or family. Suite is outfitted with pri ...
From $221 per night (USD)
VRBO
From $674 per night (USD)
VRBO
Modern Styled Home in Historic Annapolis Eastport Neighborhood
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Built in 2021 and freshly styled in 2025 with a unique modern European touch, our family-friendly retreat offers the per ...
From $674 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Waterfront lux cottage with amazing views near DC
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Rowan's Rendezvous! Relax with the whole family at this renovated 1930's bungalow. This waterfront front ...
From $363 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Charming 3-bedroom house in Annapolis Eastport! Beautifully furnished home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully furnished 3 bedroom, 2 bath home, available for short or long term rental in Eastport Annapolis! 4 minutes ...
From $511 per night (USD)
VRBO
From $710 per night (USD)
Expedia
Beautiful Historic Flat next to City Dock + USNA
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Just steps from Main Street, City Dock, and the USNA (300 ft), you'll be in the perfect location for exploring Annapolis ...
From $710 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Brand new beautiful in-law suite loft above garage with river View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Riva at this lovely condo. This phenomenal property features 1 bedroom with a queen bed, a cozy living room wi ...
From $321 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Shady Side, this charming 2-bedroom house offers a king bed and a queen bed for guests to relax in. With amen ...
From $479 per night (USD)
Expedia
From $460 per night (USD)
VRBO
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
SUMMARY | This charming, family-friendly home offers the perfect mix of comfort, convenience, and coastal vibes—just wal ...
From $460 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Entire house minutes away from BWI airport, close to Annapolis, Baltimore, DC
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
Send me an inquiry if you intend to rent a house for 3 weeks or more to inquire about a discount. Experience unbeatable ...
From $525 per night (USD)
VRBO
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 $535 per night (USD)
VRBO
Pet Friendly | Park Free & Walk to USNA Stadium
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: This is the Annapolis home your group has been looking for. Four bedrooms, 2 baths, and room for 10 — plus a p ...
From $535 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Captains Quarters | Waterfront & Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to Captains Quarters — your waterfront home in the Yacht Club Condominiums. Fall asleep to the sound o ...
From $371 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Pet-Friendly Eastport | Yard & Fire Pit
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Bring your dog, grab a drink, and settle into this 2-bedroom Eastport home with a private fenced backyard buil ...
From $374 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Cozy 3-bedroom condo with WiFi, AC in fabulous Hanover pet and family friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Your Hanover adventure begins at this marvelous 3-bedroom condo. Inside, you'll find a king bed, twin bed, full bed, and ...
From $472 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Water view Oasis renovated 3 bedrooms, 2.5 bath &hot tub conveniently in Arnold!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience Arnold like a local in this 3-bedroom house. This peaceful retreat offers 1 king bed and 3 queen beds, perfec ...
From $567 per night (USD)
VRBO
From $620 per night (USD)
VRBO
Cozy Stay in Downtown Naptown -Located in the heart of Annapolis - 3BR, 2 BA
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to 17 Lafayette Ave—your charming retreat in the heart of historic Annapolis! Just steps from downtown, the U.S. ...
From $620 per night (USD)
VRBO
From $503 per night (USD)
VRBO
Spacious 4BR | Pet-Friendly, Sleeps 10
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Spread out in this spacious 4-bedroom Annapolis home — room for 10 with an open layout, updated finishes, and ...
From $503 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Pool Loft Suite | Bay Access & Beach Passes
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
Summary: Private loft suite in the Cape St. Claire/Broadneck area with shared pool access, community beach passes, and ...
From $503 per night (USD)
Expedia
From $709 per night (USD)
VRBO
Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Mar ...
From $709 per night (USD)
VRBO
From $560 per night (USD)
Expedia
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)
Expedia
From $463 per night (USD)
VRBO
Dean Street's Lower Deck House!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Welcome to our charming 1-bedroom retreat in the heart of Annapolis’ Historic District! Just steps from shops, ...
From $463 per night (USD)
VRBO
From $573 per night (USD)
VRBO
Waterfront | Pool, Dock & Sleeps 12
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Summary: Your private waterfront escape. Dive into the pool, fish off the dock, or watch the sunset over the Chesapeake ...
From $573 per night (USD)
VRBO
From $531 per night (USD)
VRBO
DTA 2 bdrm w/parking, pet friendly, great location with all of the amenities!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This 2-bedroom non-investor house has everything you need for a great stay! We live there part time so it’s not an empty ...
From $531 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Coastal Modern Retreat | Large Group Getaway on 2 Acres
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Summary: Welcome to Coastal Modern Retreat, your ideal family and group getaway in beautiful Arnold, MD! This spacious ...
From $736 per night (USD)
Expedia
From $834 per night (USD)
VRBO
Upscale Escape with Private Garden-Perfect for Relax & Intimate Moments
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Stay comfortably in Sun Valley at this beautiful posh 5-bedroom house. With an open concept/contemporary, 2 king beds, 2 ...
From $834 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 $705 per night (USD)
VRBO
Experience Historic Annapolis Stay in This Unique Dual-Suite Home with On-Site Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Experience the Difference: Professionally Managed by iTrip Annapolis Stay right in the heart of Historic Annapolis, jus ...
From $705 per night (USD)
VRBO
From $696 per night (USD)
Expedia
Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Elegant Historic Home with Private Parking in the ...
From $696 per night (USD)
Expedia
From $431 per night (USD)
VRBO
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Coastal Elegance at FLOHOM 14 | Soteria ✨ Welcome aboard FLOHOM 14—a contemporary, coastal-inspired luxury hou ...
From $431 per night (USD)
VRBO
From $1008 per night (USD)
VRBO
Annapolis Area Gem for Family and Friends
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Large, spacious home perfect for family gatherings and special events. Whether you are attending the 50th season of the ...
From $1008 per night (USD)
VRBO
From $445 per night (USD)
VRBO
Annapolis Town Center Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Escape to our charming 2-bed, 2-bath cottage in Annapolis Town Center! Newly updated, this cozy retreat comfor ...
From $445 per night (USD)
VRBO
From $559 per night (USD)
Expedia
Historic Row Home in Downtown Annapolis
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church a ...
From $559 per night (USD)
Expedia
From $551 per night (USD)
VRBO
Upscale Condo in Annapolis w/Private Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the West Street Hideaway. See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation re ...
From $551 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Cozy and modern renovated Bayfront home with private pier and amazing views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Deale is waiting for you at this modernized 2-bedroom bungalow. Nestled in a picturesque waterfront setting, this fantas ...
From $238 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Spacious & beautiful 4-bedroom in a peaceful Severn, close to DC & Baltimore
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Relax in this spacious, single-level 4BR, 3BA home in Severn, MD—just minutes from Fort Meade, BWI, Arundel Mills & DC. ...
From $505 per night (USD)
VRBO
From $923 per night (USD)
VRBO
Wonderful Cottage Nestled On Chesapeake Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Stunning home a short walk from Chesapeake Bay - a perfect blend of comfort and coastal charm. Stroll, jog or bike in th ...
From $923 per night (USD)
VRBO
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 $1357 per night (USD)
Expedia
Annapolis History In Style Next to City Dock with Street Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to the historic Strohm House, just half a block from Main Street and the City Dock, with the U.S. Naval Academy ...
From $1357 per night (USD)
Expedia
From $337 per night (USD)
VRBO
Beautiful 2-bedroom water view house in Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this beautifully renovated cottage overlooking the Chesapeake Bay. Just steps from a serene public beach, this ...
From $337 per night (USD)
VRBO
From $448 per night (USD)
VRBO
A Little Piece of Paradise - Waterfront Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
About this space Unobstructed views of the Chesapeake Bay!! Wake up to beautiful sunrises, take a walk/run by the Bay, ...
From $448 per night (USD)
VRBO
From $277 per night (USD)
VRBO
3-bedroom house in Gambrills, in the area of Annapolis, Baltimore, & DC.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Consider this house your home away from home while you visit Gambrills, Md. This beautiful 3 bedroom, 1 level rancher ...
From $277 per night (USD)
VRBO
From $797 per night (USD)
VRBO
3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Close to US Naval Academy (1.6 mi.), Navy-Marine Corps Memorial Stadium (1.1mi), and Anne Arundel Medical Center (less t ...
From $797 per night (USD)
VRBO
From $412 per night (USD)
VRBO
Renovated 3BR | Near Sandy Point Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This renovated 3-bedroom home is 2 miles from Sandy Point State Park and 7 miles from Downtown Annapolis. Gril ...
From $412 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 $632 per night (USD)
Expedia
Boutique Cedar Home 2 blocks from City Dock, USNA & Main Street w Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the Difference: Professionally Managed by iTrip Annapolis Step into Annapolis history at this beautifully re ...
From $632 per night (USD)
Expedia
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 $386 per night (USD)
Expedia
Luxury 3-bed Townhome W/Modern finishes & Easy access to Baltimore &Annapolis.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home in the heart of Glen Burnie’s desirable Primrose community. This beautifully designe ...
From $386 per night (USD)
Expedia
From $863 per night (USD)
VRBO
Newly Renovated 2-Bedrom Eastport Home - Park in the Drive and Walk to Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautifully renovated home in Eastport one of Annapolis’s sought after neighborhoods. Two blocks from the Spa Creek Brid ...
From $863 per night (USD)
VRBO
From $455 per night (USD)
VRBO
Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Boat show vendors and visitors!!! This quiet waterfront Annapolis apartment features a queen bed, double futon, Full ki ...
From $455 per night (USD)
VRBO

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