Annapolis Vacation Rentals, Homes, & More

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Annapolis Maryland Vacation Rentals - Cottage
1 / 19

Annapolis Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$260

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$260 - $525
Per week:$1,200 - $1,775
Pets allowed:No
Internet:Yes

Waterfront timber frame large cottage in Annapolis, MD. Private, wooded setting with excellent views. Please inquire to the property owner for rates and quote. This house is an energy efficient 9 year old house perched atop a small bluff overlooking picturesque Mill Creek...

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Annapolis Maryland Vacation Rentals - Home
1 / 24

Annapolis Home
4 Bedrooms / 4 Bathrooms / Sleeps 14

from

$850

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:14
Type:Home
Per night:$850
Per week:$5,950
Pets allowed:Yes
Internet:Yes

A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. This incredible home has 100’ of floor- to- ceiling windows nestled in the tree canopy for expansive views of Weems Creek. Decks span the entire house 65' above the water. There are 4 full...

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1 / 13

Annapolis Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 8

from

$400

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:8
Type:Home
Per night:$400 - $600
Per week:$2,600 - $3,000
Pets allowed:Yes
Internet:Yes

NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul ...

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relax on the deck
1 / 12

Annapolis Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”9 Reviews

from

$250

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$250 - $300
Per month:$7,500 - $9,000
Pets allowed:No
Internet:No

Fredelig sted"(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine and birch wood inside. The bright panoramic view of the Chesapeake from the great room, master bedroom or deck elicits a relaxed, peaceful mood as soon as you...

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Wonderful!

“ Excellent ”
May 7, 2014
Our family had a wonderful visit to Deale, MD. The house was perfect and the setting was just beautiful looking over the Chesapeake Bay. Would have liked to enjoy the home more but was in town for a family wedding. Hope to come back.
Shelly Flynn, Asheville, NC USA

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Annapolis Maryland Vacation Rentals - Home
1 / 17

Annapolis Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”7 Reviews

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$300 - $350
Per month:$9,000 - $10,500
Pets allowed:No
Internet:Yes

You'll love the stunning 180- degree view of the South River, just off the Chesapeake Bay near Annapolis. The location is incredible. Just six miles from Annapolis and the United States Naval Academy. The home is 15 miles from Baltimore/Washington International Airport and 40 minutes...

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Look no further....Absolutely Perfect

“ Excellent ”
October 30, 2014
Stayed here Columbus Day weekend. Loved loved loved it. Wish we could have stayed the week...or longer. The views of the river and the boats sailing by were divine. We did go to Annapolis , a short drive away. It was nice enough but I couldn't wait to get back to our haven near the city. It was so nice to see that areas like this one still exist and that they haven't all been plowed over and replaced by huge new places.The house itself has everything you need. We ate dinners out but enjoyed breakfasts with a view. Plenty of room, comfy beds and living areas , decks all around.
Sue Roach, Long Island , New York

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Annapolis, MD Travel Tips

Located off of the Chesapeake Bay, Annapolis, MD, is a vacation destination that’s full of historic charm. This vibrant city is also a great place for families who love being in and around the water. A fantastic way to appreciate the atmosphere and “feel” of Annapolis is to stay among the locals during your trip. To do that, let Vacation Home Rentals help you choose from the best rental homes in Annapolis, MD. We have some of the most well-maintained and affordable vacation rentals Annapolis, MD, has to offer. Listed right here online, you’ll find for-rent-by-owner properties that have everything you and your family will need. Finding the right rental is only the first step when it comes to scheduling the perfect Annapolis vacation. Consider the weather when planning and preparing for your vacation. This is a valuable tip that can save you time and discomfort. Prepare for potential rain by packing rain gear, as the town receives three or more inches of rain on a monthly basis. Temperatures average as low as 44 degrees Fahrenheit in January to 90 degrees Fahrenheit in July.
Attractions
When staying in one of the Annapolis vacation rentals, you’ll want to visit the U.S. Naval Academy. Take a guided tour of this active training facility, and don’t forget to visit the Naval Academy Museum, which is also a must-see. The city’s many museums and memorials are also great attractions for families staying in Annapolis rental homes. This includes the Banneker-Douglass Museum and the Annapolis Maritime Museum. The Banneker-Douglass Museum is an African-American heritage museum that displays Maryland’s African-American history. Located at the harbor where slave ships arrived carrying their human cargo is The Kunta Kinte-Alex Haley Memorial. This is another educational spot for families, who can take photographs with the sculptures. Another memorial and statue to visit while in the city is the Thurgood Marshall Memorial.
Outdoor activities and attractions can lead to tranquil afternoons of fun for all. Quiet Waters Park has trails for biking and/or hiking, playgrounds for children, and even a skating rink. Sandy Point State Park is a year-round park that is near the Chesapeake Bay. Many visit the area for its amazing beaches and water views, but there are also boating, crabbing, picnics, and more. Although Annapolis house rentals are relaxing, a trip to Jonas Green State Park is also refreshing. A walking tour through downtown Annapolis is yet another relaxing experience for families.
Events
There is no better time than during an event for families to stay in Annapolis home rentals. These events take place at various times throughout the year. In March, for example, Annapolis celebrates Maryland Day. In May, the Annapolis Maritime Festival is the event to attend. During the summer, Annapolis vacation rentals are perfect for families as there are plenty of events to enjoy. Don’t miss the Irish Festival in June, or the City of Annapolis Fourth of July Fireworks spectacular in July. August brings the Annapolis Art Walk and the Annapolis Crab Feast to town. Around mid-September, the Fall Festival takes place in historic Annapolis. Oktoberfest comes to West Annapolis in October along with the annual Annapolis Halloween Festival. December turns the town extra-magical, making Annapolis house rentals the perfect place to be. The Lighting of the Holiday Tree festivities and the Annapolis Boat Parade of Lights set a festive mood that is not to be missed.
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