Anne Arundel Area Rentals
From $386 per night (USD)VRBO
Entire Home in Glen Burnie - 3 Bedroom Fully Fenced
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a cozy stylish experience at this centrally-located place. This is a charming private, family friendly 3 bdroom w/ ...
From $386 per night (USD)VRBO
From $540 per night (USD)VRBO
Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Contact us for discounted monthly rates! The Chesapeake Bay area is beautiful in the colder months. Consider this hous ...
From $540 per night (USD)VRBO
From $787 per night (USD)VRBO
Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Eastport Cape Cod – Walk to Downtown Annapolis ...
From $787 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 $297 per night (USD)VRBO
Private Severna Park Getaway Near Annapolis!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy the very best of Severna Park from the comfort & convenience of this upgraded private retreat! Perfectly situated ...
From $297 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 $347 per night (USD)VRBO
1 Block to USNA Stadium: Modern Annapolis Home!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Central Location | New Build | In-Unit Laundry | Fire Pit | 2 Mi to USNA Settle into this Annapolis vacation rental tha ...
From $347 per night (USD)VRBO
From $322 per night (USD)VRBO
Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Quiet furnished, double bed, kitchenette, private full bathroom quiet and private studio in home 10 minutes from Downto ...
From $322 per night (USD)VRBO
From $286 per night (USD)VRBO
Stunning 2-Bedroom loft apartment in waterfront community near BWI
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
*Cozy 2BR Loft in Point Pleasant* Enjoy a stylish loft with full kitchen, queen bed +daybed with trundle that turns int ...
From $286 per night (USD)VRBO
From $559 per night (USD)Expedia
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)Expedia
From $87 per night (USD)VRBO
Charming 2-bedroom house with fitness room and AC in Glen Burnie
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this lovely house in picturesque Glen Burnie. This cozy retreat features 2 soothing bedrooms with queen beds, ...
From $87 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 $1887 per night (USD)VRBO
Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Your Fun Filled getaway awaits in Annapolis at this Phenomenal Waterfront House with Hot Tub! With 5 bedrooms including ...
From $1887 per night (USD)VRBO
From $323 per night (USD)Expedia
The Red Door Cottage in Eastport - Pet-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This stylish, pet-friendly boho retreat is just 1 mile from downtown Annapolis and Eastport’s restaurants—your perfect h ...
From $323 per night (USD)Expedia
From $397 per night (USD)VRBO
Modern Gem Near Historic Annapolis & Naval Academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Built in August 2025 | Group-Friendly Layout w/ 4 En-Suite Bedrooms | 1 Mi to Shopping, Dining & Hospitals Spacious and ...
From $397 per night (USD)VRBO
From $393 per night (USD)VRBO
Paradise of Pasadena
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Consider this house your home away from home while you visit Pasadena. With 3 bedrooms including brand new mattress,2 ki ...
From $393 per night (USD)VRBO
From $228 per night (USD)VRBO
Modern Comfort Cozy Living & Calm, Stylish Design - Entire Home 12 Min to BWI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your fully renovated modern retreat in Glen Burnie, just 12 minutes from BWI Airport! This stylish home sle ...
From $228 per night (USD)VRBO
From $1032 per night (USD)VRBO
Beautiful Historic Annapolis home just a few minutes walk from Main Street
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming Historic Annapolis Candlelight and Secret Garden tour home, built in 1879, with gorgeous heart pine floors. Cus ...
From $1032 per night (USD)VRBO
From $388 per night (USD)VRBO
Classic 3 Bedroom Eastport Cottage with Large Yard and Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the perfect Annapolis getaway in this charming three bedroom Eastport cottage. Ideally located just ...
From $388 per night (USD)VRBO
From $1650 per night (USD)VRBO
Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to your private waterfront escape on Lake Ogleton, where relaxed luxury meets classic Chesapeake Bay living. Thi ...
From $1650 per night (USD)VRBO
From $334 per night (USD)VRBO
The Corner House-Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Updated and newly furnished home in Annapolis! Excellent location to everything Annapolis has to offer---walking distanc ...
From $334 per night (USD)VRBO
From $831 per night (USD)Expedia
Bayberry Retreat on the Magothy River. Minutes to Downtown Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Bayberry Retreat, a comfortable and spacious home in Arnold’s Bayberry community, just minutes from historic ...
From $831 per night (USD)Expedia
From $141 per night (USD)VRBO
Cozy 2-bedroom condo in Maryland City
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located in Maryland City, this condo is a dream. Guests will find two comfortable bedrooms, featuring one queen bed and ...
From $141 per night (USD)VRBO
From $232 per night (USD)VRBO
Cozy 1-bedroom cottage in adorable Annapolis on a private wooded area
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the beauty of Annapolis from this 1-bedroom cottage. Guests enjoy a soothing space featuring a comfortable quee ...
From $232 per night (USD)VRBO
From $2153 per night (USD)VRBO
Marvelous Home with Backyard Living Room in Murray Hill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
From $2153 per night (USD)VRBO
From $2073 per night (USD)VRBO
Beautiful 6 BR home on quiet secluded lot overlooking the Severn River
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
STR00749 - Heaven on the Severn This beautiful 4000 square foot Nantucket style home situated on an expansive private lu ...
From $2073 per night (USD)VRBO
From $634 per night (USD)VRBO
Modern 4BR Severn Home • 10 Min to BWI • Near Fort Meade • Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Bring the whole family and enjoy space, comfort, and convenience at this modern 4-bedroom home in Severn, Maryland — lo ...
From $634 per night (USD)VRBO
From $310 per night (USD)Expedia
Entire house in serene Pasadena with outdoor living, game room, and home office.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 12
Welcome to your ultimate home away from home! Whether you are planning a multi-family vacation, a relaxing weekend getaw ...
From $310 per night (USD)Expedia
From $480 per night (USD)VRBO
Rose Haven Coastal Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Unwind in comfort at this charming 3 bedroom, 2 bathroom beach cottage, ideally located in the heart of Rose Haven. Whe ...
From $480 per night (USD)VRBO
From $268 per night (USD)Expedia
Modern Luxury Townhome - 2BR/2BA Near Fort Meade & BWI - Private Driveway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Jo’s Luxury Retreat is a modern and comfortable place designed for relaxing, working, or exploring DC, Maryland, and Vir ...
From $268 per night (USD)Expedia
From $371 per night (USD)VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to my home! This open concept 3 (2 queens and 1 king) 2.0 full bath cottage has a large, fenced yard and backs ...
From $371 per night (USD)VRBO
From $1316 per night (USD)Expedia
Stunning 5-bedroom house near Annapolis, available for May 2026 rental
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Consider this house your home away from home while you visit Annapolis for Commissioning Week. Located in nearby Severn ...
From $1316 per night (USD)Expedia
From $315 per night (USD)VRBO
The Retro Pad
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in Glen Burnie, this delightful building offers 3 cozy bedrooms - two bedrooms with a double bed and the owners ...
From $315 per night (USD)VRBO
From $483 per night (USD)Expedia
4BR Family Retreat Near Annapolis w/ Large Yard
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully updated 4-bedroom home in The Anchorage waterfront community is just 12 minutes from downtown Annapolis ...
From $483 per night (USD)Expedia
From $463 per night (USD)VRBO
Charming WATERFRONT 3BR/2BA cottage - 20 mins to Annapolis/40 mins to downtwn DC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Your Chesapeake Bay vacation begins at this 3-bedroom cottage retreat just a short drive to Annapolis (20 mins) and down ...
From $463 per night (USD)VRBO
From $1698 per night (USD)Expedia
8,000 Sq Ft Luxury Estate Near Annapolis | Sleeps 32 | Pool, Theater & Pickleball
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 32
Welcome to your private 11-acre luxury getaway in Davidsonville, Maryland, just 10 minutes from Annapolis, 30 minutes fr ...
From $1698 per night (USD)Expedia
From $322 per night (USD)VRBO
2-bedroom house in nice Annapolis with cool AC breeze
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your cozy getaway awaits in Annapolis at this lovely house. With two comfortable bedrooms featuring a king bed and a ful ...
From $322 per night (USD)VRBO
From $755 per night (USD)VRBO
Cozy Waterfront Retreat w/ Dock, Hot Tub, Fire Pit, Game Room, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Picture yourself waking up to peaceful waterfront views, sunlight dancing on the water, and a spacious fenced yard just ...
From $755 per night (USD)VRBO
From $174 per night (USD)VRBO
Chic Laurel Extended Stay:Near Ft Meade•BWI•NSA
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
**LONG TERM LEASING ONLY*** A beautifully updated, modern home designed for comfort, work, and long-term living. Locate ...
From $174 per night (USD)VRBO
From $663 per night (USD)Expedia
Welcome to Getaway on the Bay | Your Waterfront Annapolis Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Water views. Room to gather. Coastal Maryland charm. Your perfect Annapolis getaway starts here. Welcome to Getaway on t ...
From $663 per night (USD)Expedia
From $635 per night (USD)VRBO
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax at this quiet 3BR, 2BA Annapolis retreat just minutes from downtown and the waterfront. Walk to nearby shops and c ...
From $635 per night (USD)VRBO
From $1580 per night (USD)Expedia
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis' histor ...
From $1580 per night (USD)Expedia
From $1917 per night (USD)VRBO
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience ...
From $1917 per night (USD)VRBO
From $610 per night (USD)Expedia
Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This bright and inviting vacation home provides an ideal escape for a romantic couple's getaway or a family excursion, a ...
From $610 per night (USD)Expedia
From $634 per night (USD)VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Conveniently located in the Historic District of downtown Annapolis, this two-story retreat is perfect for families and ...
From $634 per night (USD)VRBO
From $615 per night (USD)Expedia
Splendid home w/private pool, fire pit, several decks & balconies
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to this stunning five-level house nestled on a quiet and expansive 5-acre property in Annapolis, MD. With decks o ...
From $615 per night (USD)Expedia
From $1007 per night (USD)VRBO
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, an ...
From $1007 per night (USD)VRBO
From $680 per night (USD)Expedia
Splendid dog friendly home within walking distance to beach & play area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this charming house in Edgewater, MD, where a beach and play area are just a short walk away. With a water vie ...
From $680 per night (USD)Expedia
From $747 per night (USD)VRBO
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for the perfect retreat for a memorable stay-cation with your beloved groups? Then, look no further than this tw ...
From $747 per night (USD)VRBO
From $2175 per night (USD)Expedia
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Find gorgeous gathering spaces inside and out at this light-filled three-story waterfront home on a protected inlet of t ...
From $2175 per night (USD)Expedia
From $1075 per night (USD)VRBO
Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Overlooking Chesapeake Bay, this charming Annapolis home is nestled in the serene Bay Ridge community, just steps away f ...
From $1075 per night (USD)VRBO
From $1477 per night (USD)Expedia
Spacious home with an outdoor pool, screened porch, washer/dryer & central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in a family neighborhood between Fishing Creek and the South River, this Annapolis vacation home is great for gr ...
From $1477 per night (USD)Expedia
From $1713 per night (USD)VRBO
Renovated, dog-friendly home with private pool, hot tub & stunning backyard
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Whether you're planning to explore Annapolis, Baltimore, or Washington, DC, this four-bedroom home in Pasadena perfectly ...
From $1713 per night (USD)VRBO
From $1064 per night (USD)Expedia
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This newly updated mid-century modern home offers a peaceful retreat from the brisk pace of everyday life. The home sits ...
From $1064 per night (USD)Expedia
From $548 per night (USD)VRBO
Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great wa ...
From $548 per night (USD)VRBO
From $572 per night (USD)Expedia
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Historical charm meets modern convenience at this darling brick home, within easy walking distance of all Annapolis' cha ...
From $572 per night (USD)Expedia
From $508 per night (USD)VRBO
Serene waterfront home with kayaks, paddle board, grill, firepit, W/D, and AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled right on Severn River's shoreline, this waterfront retreat has been completely remodeled, redecorated, and boast ...
From $508 per night (USD)VRBO
From $1160 per night (USD)Expedia
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready fo ...
From $1160 per night (USD)Expedia
From $1940 per night (USD)VRBO
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
On the quiet Lake Ogleton off of the Chesapeake, this waterfront home with a gorgeous new pool, hot tub, and private pie ...
From $1940 per night (USD)VRBO
From $987 per night (USD)Expedia
Waterfront Annapolis Home Near USNA Stadium
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your waterfront Annapolis getaway! This inviting 3-bedroom home comfortably sleeps 6 and offers pea ...
From $987 per night (USD)Expedia
From $190 per night (USD)VRBO
Modern 1 bedroom - deck and water view, pet-friendly, water-privileged w beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lovely upper floor above a newly built detached garage. Spacious, safe neighborhood with a community beach and multiple ...
From $190 per night (USD)VRBO
From $286 per night (USD)Expedia
Water's Edge 2-bedroom house in charming Edgewater
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Edgewater at this terrific house. With two cozy bedrooms featuring queen beds, guests find plenty of space to ...
From $286 per night (USD)Expedia
From $806 per night (USD)VRBO
Waterfront Retreat Private Pier and Sunset Views
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: A waterfront home on Cadle Creek with its own pier and boat slip, a wide west-facing deck, and sunsets over th ...
From $806 per night (USD)VRBO
From $773 per night (USD)Expedia
Walk to Herrington Harbor: Spacious Bay Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
4,180 Sq Ft | Private Setting on a Wooded Lot | < 1 Mi to Marina | Library Tucked into the Traceys Creek community, thi ...
From $773 per night (USD)Expedia
From $480 per night (USD)VRBO
Port of Call: 5BR Modern Nautical Luxury
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to your Annapolis basecamp! Located in the private Anchorage community, by Annapolis Cove - a quick 12 minutes t ...
From $480 per night (USD)VRBO
From $698 per night (USD)Expedia
Annapolis Charmer - Perfect Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Enjoy a stylish stay in this beautifully updated, centrally located home featuring brand-new furnishings and a ...
From $698 per night (USD)Expedia
From $569 per night (USD)VRBO
6BR 3 Bath Waterfront Home w/ Private Dock & Views
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Waterfront escape with room for everyone! This spacious 6BR/3BA home offers serene water views, a private dock for kayak ...
From $569 per night (USD)VRBO
From $744 per night (USD)VRBO
Historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
RENT-005995-2024-The Campbell House on Prince George offers the best of downtown Annapolis with a rare blend of historic ...
From $744 per night (USD)VRBO
From $577 per night (USD)VRBO
Location=AMAZING! Garage Parking for 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Yes! It really is the Perfect Vacation Rental in Annapolis!----Discover the perfect blend of historic charm and contemp ...
From $577 per night (USD)VRBO
From $1192 per night (USD)VRBO
Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
STR-250 -Escape to this spacious waterfront home in Arundel on the Bay, where sweeping Chesapeake Bay views surround you ...
From $1192 per night (USD)VRBO
From $732 per night (USD)VRBO
3 BR charming home sits in the heart of Annapolis with rooftop deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STR-144253 Welcome to The Yellow Door on Cornhill, a beautifully restored 1800 brick home in the heart of downtown Anna ...
From $732 per night (USD)VRBO
From $462 per night (USD)VRBO
Historic District 2BR + Parking | Walk to City Dock & USNA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Stay in the heart of Annapolis’ Historic District, just a short walk from City Dock, the U.S. Naval Academy, restaurants ...
From $462 per night (USD)VRBO
From $359 per night (USD)VRBO
Private 2BR Apartment with Parking for Corporate, Medical & Military Stays
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR-270 - This private 2-bedroom apartment in Annapolis is a smart choice for mid-term renters seeking a clean, comforta ...
From $359 per night (USD)VRBO
From $1475 per night (USD)VRBO
Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR000259 - Just minutes from downtown Annapolis, this stunning waterfront home offers a private, upscale retreat for up ...
From $1475 per night (USD)VRBO
From $522 per night (USD)VRBO
Historic Downtown Annapolis | 2BR En Suites | Walk to USNA & City Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in the heart of historic downtown Annapolis at this charming 2-bedroom, 2.5-bath townhome on quiet Pinkney Street. ...
From $522 per night (USD)VRBO
From $353 per night (USD)VRBO
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RENT-000642-2025- Experience unparalleled ease and convenience to downtown Annapolis with this exquisite top-floor corn ...
From $353 per night (USD)VRBO
From $635 per night (USD)VRBO
Spacious 4BR Annapolis Home | Near Navy Stadium & Downtown | Sleeps 9
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
STR-270 - Traveling to Annapolis with family or friends? Quiet Quarters offers the space, convenience, and comfort of a ...
From $635 per night (USD)VRBO
From $1249 per night (USD)Expedia
Eastport 4 Bedroom Spacious Gem on Jefferson
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to our newly updated 4-bedroom home in the charming Eastport area of Annapolis! This spacious retreat ...
From $1249 per night (USD)Expedia
From $515 per night (USD)VRBO
Chapel Gate 3BR Steps to City Dock & Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Chapel Gate! Ideally located just outside Gate 3 of the U.S. Naval Academy and only a few blocks fr ...
From $515 per night (USD)VRBO
From $1359 per night (USD)Expedia
This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Ogelton Overlook. This 5 bedroom / 5 bathroom Coastal Charm sleeps 14 comfortably. This thoughtfully stylish ...
From $1359 per night (USD)Expedia
From $2441 per night (USD)VRBO
Gorgeous 6-bedroom Charming Annapolis Retreat
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Make yourself at home in this 6-bedroom Annapolis house. With 4 queen beds and 2 king beds, there’s plenty of space for ...
From $2441 per night (USD)VRBO
From $246 per night (USD)Expedia
Charming 1-bedroom cottage with AC in cozy Harwood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the beauty of Harwood from this 1-bedroom cottage.Located a short distance from Annapolis or Washington,DC it i ...
From $246 per night (USD)Expedia
From $576 per night (USD)VRBO
Luxury Spa Retreat Severn Hot Tub & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Private Luxury Spa Retreat in Severn, Maryland. This elegant 3-bedroom home blends comfort, privacy, and upscale relaxat ...
From $576 per night (USD)VRBO
From $334 per night (USD)VRBO
Private & Quiet Cottage in West Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy, bright & private cottage in woods w easy access to town & highways; front porch & screened-in back deck w rocking ...
From $334 per night (USD)VRBO
From $514 per night (USD)VRBO
Downtown Annapolis 3 bedroom home with parking!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Our 3 bedroom home is close to everything in Annapolis, making it easy to plan your visit. Walk to downtown re ...
From $514 per night (USD)VRBO
From $483 per night (USD)VRBO
Private Retreat Severn, Fire Pit & Gazebo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This private luxury spa retreat is designed for deep relaxation, featuring inviting living areas with cozy seating and s ...
From $483 per night (USD)VRBO
From $1188 per night (USD)VRBO
2 Home, Private Luxury Retreat, Sleeps 20
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 9
Escape to a private luxury spa retreat in Severn, Maryland, just minutes from DC. Relax in the hot tub, gather around th ...
From $1188 per night (USD)VRBO
From $610 per night (USD)Expedia
Charming Coastal Retreat w Community Beach Dog-Friendly & Mins to Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis Family and Dog-Friendly Coastal Retreat | Walk to ...
From $610 per night (USD)Expedia
From $182 per night (USD)VRBO
Private Modern Tiny Home Near BWI Baltimore
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inside, you'll find a comfortable king-size bed, a sofa bed, and the option to request a pack-and-play for little ones. ...
From $182 per night (USD)VRBO
From $482 per night (USD)VRBO
Modern Tiny Home with Pool Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inside, you'll find a comfortable king-size bed, a sofa bed, and the option to request a pack-and-play for little ones. ...
From $482 per night (USD)VRBO
From $837 per night (USD)VRBO
Historic Bayfront Retreat - 4BR - Stunning Chesapeake Views - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Bay Dreams, a beautiful historic home once known as the Waterfront Inn of Holland Point. Nestled along the C ...
From $837 per night (USD)VRBO
From $726 per night (USD)Expedia
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Relax after a fun Annapolis day in this well-appointed and spacious home. Centrally located in peaceful Murray ...
From $726 per night (USD)Expedia
From $431 per night (USD)VRBO
Cozy 3-bedroom cottage in water-privileged community minutes from Annapolis, MD
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in this charming home, just minutes away from Annapolis and the BWI airport. After your adventures to Annapolis ...
From $431 per night (USD)VRBO
From $751 per night (USD)Expedia
Eastport 3 bedroom Cottage: Walk to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Discover Annapolis from our charming Eastport cottage! This updated home comfortably sleeps 8 and is perfect f ...
From $751 per night (USD)Expedia
From $167 per night (USD)VRBO
Spacious 4-bedroom house with AC in brilliant Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Unwind in Annapolis at this pleasant house perfect for groups or families. With four bedrooms, including three queen bed ...
From $167 per night (USD)VRBO
From $506 per night (USD)Expedia
Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 10
Discover the beauty of Annapolis from this fantastic 5-bedroom house. With two queen beds and a peaceful bathroom featur ...
From $506 per night (USD)Expedia
From $686 per night (USD)VRBO
The Bachelorette- Wake up to waves live in luxury Your East Coast escape awaits.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to the Bachelorette! This bay front home was designed to offer a truly luxurious vacation experience for up to 8 ...
From $686 per night (USD)VRBO
From $154 per night (USD)Expedia
Cozy 1-bedroom studio in pleasant Crofton with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your cozy getaway awaits in Crofton at this pleasant studio. This perfect spot features one comfortable studio and a cle ...
From $154 per night (USD)Expedia
- From $619 per night (USD)
VRBO
Walk to everything! Downtown Historic Annapolis “Arts District”
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
None delete delete delete delete delete delete delete delete delete delete delete delete delete deletebbbbbbvvvvvvvvvggg ...
From $619 per night (USD)VRBO
From $877 per night (USD)Expedia
Luxury Waterfront Home w Private Pier in Annapolis & Dog-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to All Decked Out, your dream escape in th ...
From $877 per night (USD)Expedia