Search Vacation Homes in Annapolis

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Vacation Homes in Annapolis

Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Arundel on the Bay

9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$416 nightly
The price is $474
Dec 8 - Dec 9
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Cape Saint Claire

9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
$472 nightly
The price is $502
Dec 8 - Dec 9
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Homewood

9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$405 nightly
The price is $462
Dec 8 - Dec 9
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!

Vacation Home in Historic District

10.0 out of 10, Exceptional, (13)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
$543 nightly
The price is $581
Dec 9 - Dec 10
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Vacation Home in Admiral Heights

9.8 out of 10, Exceptional, (7)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
$460 nightly
The price is $520
Dec 15 - Dec 16
Total with taxes and fees
Cute bungalow blocks to Stadium
Marina
Cozy 2br home w/ parking in downtown Annapolis

Vacation Home in Historic District

10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$273 nightly
The price is $311
Dec 9 - Dec 10
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Vacation Home in Annapolis

9.2 out of 10, Wonderful, (16)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
United States
Mike F.
$327 nightly
The price is $372
Dec 10 - Dec 11
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$497 nightly
The price is $566
Dec 8 - Dec 9
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Microwave, oven, stovetop, dishwasher
Fabulous 5-bedroom house with AC in charming Annapolis

Vacation Home in Annapolis

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
$353 nightly
The price is $403
Dec 8 - Dec 9
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis
Fridge, microwave, oven, stovetop
Stunning 4 BR Home - Walking Distance to Stadium

Vacation Home in Homewood

10.0 out of 10, Exceptional, (1)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
$755 nightly
The price is $861
Dec 15 - Dec 16
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium
Terrace/patio
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Vacation Home in Eastport

$280 nightly
The price is $319
Dec 8 - Dec 9
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Interior
Historic Row Home 1 Block from Gate 1 at USNA!

Vacation Home in Historic District

10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$617 nightly
The price is $703
Dec 15 - Dec 16
Total with taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!
3 bedrooms, iron/ironing board, travel crib, WiFi
★ Midcentury Modern Getaway ★ Prime Location ★

Vacation Home in Historic District

10.0 out of 10, Exceptional, (35)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
United States
shannon r.
$487 nightly
The price is $556
Dec 9 - Dec 10
Total with taxes and fees
★ Midcentury Modern Getaway ★ Prime Location ★
Dining
Mins to DTA - King Beds - Parking

Vacation Home in Annapolis

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
$496 nightly
The price is $566
Dec 8 - Dec 9
Total with taxes and fees
Mins to DTA - King Beds - Parking
Fridge, microwave, oven, stovetop
All Star Annapolis Retreat - Walk to Stadium

Vacation Home in Admiral Heights

10.0 out of 10, Exceptional, (8)
"Great house, perfect for Navy football game"
United States
Kathy N.
$683 nightly
The price is $731
Dec 8 - Dec 9
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium
Terrace/patio
Chesapeake Comfort, Annapolis.

Vacation Home in Annapolis

9.8 out of 10, Exceptional, (19)
"Great place centrally located to amenities and Navy stadium. We booked an overnite with family to attend a graduation dinner nearby. "
United States
Danielle M.
$437 nightly
The price is $498
Dec 8 - Dec 9
Total with taxes and fees
Chesapeake Comfort, Annapolis.
TV, fireplace, offices
Annapolis Baystone House

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (3)
"This was a beautiful property and I would stay here again if we travel back to the area."
United States
Katherine D V.
$662 nightly
The price is $755
Dec 8 - Dec 9
Total with taxes and fees
Annapolis Baystone House
Exterior
Modern Retreat w/ Fire Pit & Parking

Vacation Home in Annapolis

2.0 star property
$426 nightly
The price is $486
Dec 8 - Dec 9
Total with taxes and fees
Modern Retreat w/ Fire Pit & Parking
Microwave, oven, stovetop, dishwasher
Walk to the stadium! - Lighthouse on Glenwood

Vacation Home in Annapolis

10.0 out of 10, Exceptional, (6)
$286 nightly
The price is $326
Dec 8 - Dec 9
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood
Interior
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (29)
"We only had a short stay but the communication with Justin was extremely quick and responsive - very clear and a great host. The property was really clean, welcoming and perfect for our short break. "
United States
Lee B.
$726 nightly
The price is $827
Dec 9 - Dec 10
Total with taxes and fees
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Annapolis Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Rooms are in the different buildings so we needed to check in to find out where we were staying. Parking is difficult so we chose to pay for valet. Loved the location and it was convenient for Midnight Madness shopping and to great restaurants."
Carolyn Alexandra 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
233
Accommodation
314 Vacation Homes
Lowest Price
$311
Highest Price
$861

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