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VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent Annapolis reviews

  • Home Away From Home

    "We enjoyed six days in Annapolis from this comfortable, spacious property. As described, this rental is within walking distance to the Stadium, as well as a 20-25 minute walk to downtown. Within three blocks is a grocery store, bank machine, 2 casual restaurants, and quant boutiques. The property itself is light and clean, has ample space for 4 people, and comes with a well-equiped kitchen. We would rent this again in a minute."
    Guest: Laurie Date of Stay: October 2014 Review Submitted: October 21, 2014
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  • Perfect in everyway!

    "There's no better word to describe this home, everything about it was perfect in every way. It had everything we needed, was clean, and just an absolute pleasure to stay in. Some of our group went on a couple nature walks while others in our group used the nearby mall to pass some time. Carla was one of the nicest people I've ever met, she answered all of my questions without fail and was very informative and caring about our group. We were able to sit around the dining room table and eat breakfasts and dinners together without being crowded, the living area coupled with the deck gave everyone plenty of room to do what they wanted to do while still being part of the group. I would love to plan a trip in the winter to this home, I would love to see that beautiful fire place in action! Another plus side was that the house is only a 20 minute drive to and from the BCC, which is where my group was going to for 90% of our trip everyday! It was easy to navigate and flawless, plus all the shopping within a 10 minute drive was great! No one in our group could have been happier!"
    Guest: Danielle H. Date of Stay: August 2014 Review Submitted: August 14, 2014
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  • Annapolis Chesapeake Bay Charmer suitable for special family gathering indeed!!

    "We utilize VRBO for many vacation lodging needs and can say this Annapolis Chesapeake Bay home exceeded our expectations in many ways. From the cordial and hospitable property management team and owners, right down to the comfortable-clean-quite-undisturbed property and surroundings, the private beach amenities, and the accuracy of the listing description. Our weekend family wedding event was transformed from a special moment to a lifetime memory by staying here, (versus staying in an area hotel), and, if we are in Annapolis again for an extended period then we would welcome the opportunity to stay at this property again without any reservations. I would highly recommend this property to any relative or friend. We also enjoyed the unrestricted view of the Bay from the front porch, the exclusive address, and the close proximity to historic downtown Annapolis... Also loved touring the US Naval Academy. Dinner recommendations? The grill provided with this rental in the backyard, the Main Ingredient, and the "Dry Dock" Restaurant on premise at the Naval Academy. Hope you enjoy as much as we did!"
    Guest: Don Date of Stay: July 2014 Review Submitted: July 25, 2014
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  • "Royal Folly" helps make family and USNA 50th reunion huge success

    "The house, itself, is a beautifully restored historic gem, situated right across from St. John's College and within walking distance of the Naval Academy and downtown Annapolis. It was spotlessly clean when we arrived. The beds were comfortable, the amenities excellent. I brought the whole family--kids and grandkids--for my very special reunion, and there wasn't a moment of disappointment for the entire weekend. I recommend highly."
    Guest: Go Navy Beat Army Date of Stay: September 2014 Review Submitted: October 1, 2014
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Annapolis Travel Tips

Adventures Await You in Annapolis Vacation Rentals

Are you up for a pirate adventure? How about a little live, local theater? Maybe your vacation to Annapolis, Maryland includes young children so a visit to one of the best children’s museums in Maryland is on the agenda. No matter what adventures you choose, Annapolis vacation rentals are close to the action.

Treasure Hunting and Pirates Make Annapolis Vacation Rentals Famous

Make staying at Annapolis lodging a whole lot more adventurous with a visit to Pirate Adventures on the Chesapeake. Learn how to read a treasure map and find the treasure. You may even get to meet the smelliest pirate on the seven seas--Pirate Pete! All sorts of adventures await kids of all ages when you book Maryland rentals. You won’t find too many pirate adventures on your vacation so take advantage of this opportunity.

Live Theater close to Annapolis Lodging

The Colonial Players always present a fine production whether they are performing comedies or tragedies. Maryland rentals near East Street in the heart of historic Annapolis are very close to the Colonial Players who always have a new production in the works. Annapolis lodging keeps you in the thick of things so when you book Annapolis vacation rentals, make a note of the addresses so you can find nearby entertainment opportunities.

Guests of Maryland Rentals Enjoy the Children’s Museum

Don’t hang around your Annapolis vacation rentals all day. Entertain the kids with a visit to the Chesapeake Children’s Museum and get their minds and bodies working. Explore the woods surrounding Annapolis lodging, learn about turtles and trucks, and create some fine art to take back to your Maryland rentals to really jazz up your accommodations. You may even be able to sneak into one of the classes the CCM offers; just ask if there’s space for you and your kids.

Other popular and affordable Maryland vacation destinations include Ocean City Maryland rentals, Deep Creek Lake accommodation, or St Michaels MD vacation homes. You will have no problem finding an ideal vacation rental home for your next Maryland family trip.

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