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

Filter

Popular Areas

From $320 per night (USD)
VRBO
Cozy 2br home w/ parking in downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully update ...
From $320 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Adorable waterside cottage with pool Beach community
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
1920's two level cottage with multiple decks and a private inground swimming pool. This home boasts water views from eve ...
From $522 per night (USD)
Expedia
From $714 per night (USD)
VRBO
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $714 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay ...
From $339 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, an ...
From $305 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The owner has created your own slice of paradise in the Rose Haven community of North Beach. Walk to Herrington Harbour ...
From $472 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Private Cottage on gated estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapo ...
From $245 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
The Beachwood Cottage is located near Mayo, Maryland, on the western shore of the Chesapeake Bay. The property sits on R ...
From $374 per night (USD)
Expedia
From $623 per night (USD)
VRBO
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $623 per night (USD)
VRBO
Click For Pricing
Expedia
Stay at Lux Red Door Gem with 3 Parking Spots
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
The gorgeous Downtown Annapolis home was meticulously remodeled from top-to-bottom in a luxurious fashion. This fully-r ...
Click For Pricing
Expedia
From $748 per night (USD)
VRBO
Steps to Main St at Historic Home with Capital Views, Private Patio & Free Off-Site Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience Historic Annapolis in Comfort and Style This charming 4-bedroom home sits in the heart of Historic Annapolis, ...
From $748 per night (USD)
VRBO
From $662 per night (USD)
Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 c ...
From $662 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Anchor's Away in the Heart of Eastport!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Downtown in the heart of Eastport Annapolis, this first floor studio condo boasts high ceilings with lots of natural lig ...
From $298 per night (USD)
VRBO
Click For Pricing
Expedia
Entire Town House Close to DC
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This is a over 2,000sq home with 4 bedrooms and 3.5 bathrooms. It is a 3 level end unit with a patio perfect for family ...
Click For Pricing
Expedia
From $233 per night (USD)
VRBO
Cozy 1st Floor King George one bedroom apartment right across from USNA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy this one bedroom first floor apartment that's right across from Gate 2 of the U.S. Naval Academy. It's a short 1 ...
From $233 per night (USD)
VRBO
From $255 per night (USD)
Expedia
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Treat yourself to the best while in Annapolis! Gorgeous 1500 sq. ft. custom designed waterfront apartment that takes fu ...
From $255 per night (USD)
Expedia
From $428 per night (USD)
VRBO
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, g ...
From $428 per night (USD)
VRBO
From $648 per night (USD)
VRBO
Downtown Annapolis Townhome ! Beautiful!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $648 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Want to get away? Staying with us. Very relaxing.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Our tastefully appointed cottages . Peaceful and tranquil, yet close to shops and restaurants, this property is perfect ...
From $185 per night (USD)
VRBO
From $580 per night (USD)
Expedia
Mins to Annapolis from Waterfront Retreat w Stunning Views of the Bay and Bridge with Fenced-In Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks! Escape to a tranquil waterfront retreat ...
From $580 per night (USD)
Expedia
$Eastport Cottage .5 mi from Downtown Annapolis\n\n$
From $420 per night (USD)
VRBO
Eastport Cottage .5 mi from Downtown Annapolis\n\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, t ...
From $420 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular vi ...
From $259 per night (USD)
Expedia
From $647 per night (USD)
VRBO
Walk to USNA, Main St w Parking Historic Wisteria
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the ...
From $647 per night (USD)
VRBO
From $142 per night (USD)
Expedia
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Annapolis, where history and nature come together! Make yourself at home in this cozy 1-bedroom, 1-bath cond ...
From $142 per night (USD)
Expedia
$Stay \Around the corner\ from Annapolis hot spots with new King bed, fenced-in yard and parking$
From $601 per night (USD)
VRBO
Stay \"Around the corner\" from Annapolis hot spots with new King bed, fenced-in yard and parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly ...
From $601 per night (USD)
VRBO
Click For Pricing
Expedia
A Delight on Dean
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sitting on a quiet, tree lined street, this home enjoys being located in the sought after neighborhood of Murray Hill. ...
Click For Pricing
Expedia
From $504 per night (USD)
VRBO
Walkable Eastport Home with Firepit, Porch & Fenced-in Yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Welcome to your home away from home in the heart of the Maritime Republic of Eastport—a vibrant, walkable neighborhood j ...
From $504 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Waterfront Oasis of Annapolis Star
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Studio, furnished apartment above detached garage on family's sprawling property. Queen-bed, with pull out full couch. S ...
From $495 per night (USD)
Expedia
From $92 per night (USD)
VRBO
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore the best of Maryland and book a stay at this cozy 1-bed, 1-bath vacation rental home in Lothian! Nestled on a fa ...
From $92 per night (USD)
VRBO
From $716 per night (USD)
Expedia
Waterfront Cheerful 6 BR Home with Private Pier
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Welcome to this brand-new relaxing home with a private pier by the water for your getaway. It is perfect for vacations, ...
From $716 per night (USD)
Expedia
Click For Pricing
VRBO
Vacation house near Downtown Annapolis
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Enjoy a weekend away in a secluded house in a lovely neighborhood right outside Annapolis. Our house is set back from th ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Cute, cozy rancher close to down town Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private location with plenty of parking. Newly renovated bathroom, french doors open to deck; great for indoor-outdoor l ...
Click For Pricing
Expedia
From $1081 per night (USD)
VRBO
Parking for days at the unique Deep in the Heart of Annapolis with large private deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been ...
From $1081 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Harbor Breezes at Herrington Harbor
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
If you are looking for a comfortable and clean home for your stay while visiting Herrington Harbor, our beaches or other ...
From $402 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Nice 5 BDR / 3 BATH Home near BWI Airport with WIFI, Beach, Parking, Ambiance
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Business, Govt. or family trip? Riviera Beach welcomes you to this lovely, elegant, well-lit and sanitized 5 BD/3 BATH h ...
From $407 per night (USD)
VRBO
From $279 per night (USD)
Expedia
New Downtown Annapolis Condo With Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No ...
From $279 per night (USD)
Expedia
From $437 per night (USD)
VRBO
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $437 per night (USD)
VRBO
From $657 per night (USD)
Expedia
Stylish Midcentury Ranch Pet-Friendly Home Just 1.5 Miles from Navy Stadium One-Level Living
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Stylish Midcentury Ranch Just 1.5 Miles from Navy Stadium! This beautifully renovated 4BR/2BA home is perfectly located ...
From $657 per night (USD)
Expedia
From $502 per night (USD)
VRBO
💥Your Annapolis Retreat near the beach and downtown💥
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Welcome to our recently renovated retreat in Annapolis. The place is located minutes from downtown, in the neighborhood ...
From $502 per night (USD)
VRBO
From $766 per night (USD)
Expedia
Eastport Historic Firehouse with Parking, Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in ...
From $766 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Annapolis Condominium in the heart of the historic center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $295 per night (USD)
VRBO
Click For Pricing
Expedia
Chic Condo w/ Balcony in the Heart of Annapolis!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
Click For Pricing
Expedia
From $1267 per night (USD)
VRBO
Parking at Randall House Across from USNA Gate 1
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1267 per night (USD)
VRBO
From $1116 per night (USD)
Expedia
Sprawling Luxury Home on a Private Cul De Sac with Gaming Sports Bar, Big Yard Mins to Annapolis
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Spacious custom home - Perfect for Naval Academy families and long visits to Annapolis Enjoy your stay in this expansive ...
From $1116 per night (USD)
Expedia
Click For Pricing
VRBO
5 BDRM across from the USNA Stadium
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
Click For Pricing
VRBO
From $1024 per night (USD)
Expedia
Private Pier Waterfront Jolly Roger mins to DTA
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 $1024 per night (USD)
Expedia
From $573 per night (USD)
VRBO
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Annapolis Beachfront w/Bay Bridge view - Wake up to a beautiful view of the sunrise over the Chesapeake Bay. Go to sleep ...
From $573 per night (USD)
VRBO
From $499 per night (USD)
Expedia
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Charming private space in a quiet neighborhood. Live like locals and enjoy walking or biking around town. Free street p ...
From $499 per night (USD)
Expedia
From $494 per night (USD)
VRBO
Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from ...
From $494 per night (USD)
VRBO
From $655 per night (USD)
Expedia
1 Block to USNA at beautifully renovated Historic Chapel Views with back patio and off-site parking
Bedrooms:
2
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 $655 per night (USD)
Expedia
From $751 per night (USD)
VRBO
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Bedrooms:
2
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 $751 per night (USD)
VRBO
From $683 per night (USD)
Expedia
Private Patio at Charming Hanover House Across from USNA Gate 3
Bedrooms:
2
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 $683 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Tranquility Awaits
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Entire Guest House. One bedroom, one bathroom with loft. Three beds, queen, full and twin. Full kitchen, laundry, dedi ...
From $167 per night (USD)
VRBO
From $314 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 $314 per night (USD)
Expedia
From $1165 per night (USD)
VRBO
Quiet home with large yard, close to Navy Bridge.
Bedrooms:
2
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 $1165 per night (USD)
VRBO
From $384 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 $384 per night (USD)
VRBO
From $1007 per night (USD)
VRBO
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $1007 per night (USD)
VRBO
From $519 per night (USD)
Expedia
Water Views - Close to Downtown Annapolis
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city onl ...
From $519 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your dream stay nestled in the heart of Historic Downtown Annapolis! Located just 45 feet from downtown Anna ...
From $527 per night (USD)
VRBO
From $498 per night (USD)
Expedia
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 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $498 per night (USD)
Expedia
From $646 per night (USD)
VRBO
Pristine Waterfront Home with Expansive Views.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
**Monthly discounts only apply for Off-Season rentals (October-April) If relaxing in luxury on the water is what you a ...
From $646 per night (USD)
VRBO
From $569 per night (USD)
VRBO
Suite Retreat Luxurious 3 BR, 3 BathRoom Rancher has game room and house keeper.
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Looking for a luxurious short term rental that will take your breath away, look no further than our stunning Suite Retre ...
From $569 per night (USD)
VRBO
From $482 per night (USD)
VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $482 per night (USD)
VRBO
From $940 per night (USD)
Expedia
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $940 per night (USD)
Expedia
From $651 per night (USD)
VRBO
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking and gorgeous outdoor space
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $651 per night (USD)
VRBO
From $787 per night (USD)
Expedia
Brand New Spacious Luxury Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
This brand-new build luxury home in Eastport close to downtown Annapolis has everything you and your guests (up to 16 to ...
From $787 per night (USD)
Expedia
From $114 per night (USD)
VRBO
Maryland Inn King, Historic Inns, Fireplace, Elegant Dining, Waterfront Proximity
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $114 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorat ...
From $295 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Waterfront Sanctuary only 50 Min. From DC/Balt.
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
New listing on VRBO!! Please see other sites for 50+ reviews on this property. New full home renovation with gourmet ki ...
From $674 per night (USD)
VRBO
From $475 per night (USD)
VRBO
Enchanting West River Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our charming waterfront cottage nestled on the serene shores of the West River! Perfectly positioned with a 3 ...
From $475 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Walk to Everything - Historic Art’s District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
HISTORIC ANNAPOLIS/ART’S DISTRICT Built in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill ...
From $426 per night (USD)
VRBO
From $1085 per night (USD)
Expedia
On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Historic Charm Across from the Naval Academy Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-ba ...
From $1085 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Splendid dog friendly home within walking distance to beach & play area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Adventure Annapolis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $465 per night (USD)
VRBO
From $639 per night (USD)
Expedia
Experience the Chesapeake Bay Lifestyle at the Historic and Waterfront Bay Dreams
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Bay Dreams, a beautifully-restored historic home once known as the "Waterfront Inn of Holland Point." Nestled ...
From $639 per night (USD)
Expedia
From $1790 per night (USD)
VRBO
Spacious Converted Carriage House in Historic District near USNA
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax in this updated and sophisticated house near the USNA in Annapolis with the largest garden in downtown. This tranq ...
From $1790 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Stay in Historic apartment 2 blocks from Main St with parking - dog-friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Still available for Commissioning Week 2025! Stay right in the heart of Historic Annapolis, just 2 blocks from Main Str ...
From $483 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
In the heart of Annapolis, where the bay breeze blows, Stands a small cottage, the Captain's Quarters, a peaceful repos ...
From $312 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Historic dog-friendly home 2 blocks to Main St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street, and feel like you’re in a hotel suite wit ...
From $437 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Rock Creek Cottage, Waterfront, Serene Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Rock Creek Cottage. Serene views from the deck and dock of deep water Rock Creek, by the Patapsco River and C ...
From $276 per night (USD)
VRBO
From $514 per night (USD)
Expedia
3-bedroom luxury vacation townhome in charming Glen Burnie with WiFi, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get ready to relax in this 3-bedroom townhome in Glen Burnie. This brilliant property features 2 queen beds and 1 king b ...
From $514 per night (USD)
Expedia
From $1180 per night (USD)
VRBO
All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your Eastport escape! This newly decorated custom home has everything—Severn River views, a huge private ya ...
From $1180 per night (USD)
VRBO
From $122 per night (USD)
Expedia
Modern 1 Bedroom Oasis in the Center of Everywhere in Severn, Maryland
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This space has everything you need. It has a private entrance to your 1 BR, 1 BA, WD and kitchen. Centrally located in M ...
From $122 per night (USD)
Expedia
From $612 per night (USD)
VRBO
Mins to DTA - King Beds - Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gat ...
From $612 per night (USD)
VRBO
From $924 per night (USD)
Expedia
Multi-unit Waterfront Home with Private Pool and Pier Mins to Downtown Annapolis
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Welcome to this beautiful waterfront home in the quiet Cool Spring Cove of the Magothy River in Arnold, MD. Not only do ...
From $924 per night (USD)
Expedia
Click For Pricing
VRBO
Townhome steps from Main St. with private backyard patio & parking
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
Click For Pricing
VRBO
From $133 per night (USD)
VRBO
7 Mi to Baltimore: Maryland Gem w/ Shared Yard!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In-Unit Washer & Dryer | 5 Mi to Cross Street Market | 6 Mi to Oriole Park at Camden Yards Experience the best of Maryl ...
From $133 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Steps to Marinas & Shops w Parking in Eastport
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis This beautiful home is located in ...
From $461 per night (USD)
VRBO
From $735 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 $735 per night (USD)
VRBO
From $602 per night (USD)
VRBO
Less than 1 mile to Navy Stadium, Fenced-in Yard and Dog-Friendly Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
A new home but managed by experienced hosts, iTrip Annapolis, dedicated to exceptional hospitality. Discover the perfect ...
From $602 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Charming & Cozy 1-bedroom apartment newly renovated in Linthicum Heights.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located only 1.4 miles from BWI and 31 miles from DCA , this cozy & charming 1/1 accessory dwelling unit brings convenie ...
From $165 per night (USD)
Expedia
From $956 per night (USD)
VRBO
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Make yourself at home in this 5-bedroom Annapolis Waterfront Retreat. This superb house boasts 3 king beds, 1 queen bed, ...
From $956 per night (USD)
VRBO
From $583 per night (USD)
Expedia
Stay in the Heart of Annapolis on King George Street Steps to USNA Gate 1 & Main Street
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Your Historic Annapolis Retreat! Discover this newly-renovated and professionally-decorated gem on the presti ...
From $583 per night (USD)
Expedia
From $505 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 $505 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Experience the perfect blend of modern luxury and coastal charm in this stunning waterfront home on the Chesapeake Bay. ...
From $566 per night (USD)
VRBO
From $836 per night (USD)
VRBO
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 ...
From $836 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Unique and central in Eastport
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Take it easy at this unique and tranquil getaway in historic Eastport. This 4-bedroom, 3-bathroom home has plenty of spa ...
From $437 per night (USD)
Expedia
From $945 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 $945 per night (USD)
VRBO
From $167 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 $167 per night (USD)
VRBO
From $261 per night (USD)
VRBO
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 $261 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Cozy Annapolis Getaway: Firepit, Pet-Friendly, Fenced Yard, Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your Annapolis adventure starts at this spacious 3-bedroom, 2-bath home! Featuring a king, queen, and twin bed, plus a c ...
From $398 per night (USD)
Expedia

Search Your Destination Now!

Anne Arundel Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 522 Rentals