
Guest house holiday rentals in Anne Arundel County
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Top-rated guest house rentals in Anne Arundel County
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Family-friendly guest house rentals

Annapolis Guesthouse - Completely Separate Space
This unit is detached from the main house but connected by a covered walkway. The common area, kitchen, bathroom and two bedrooms are as described in the listing. It was a very comfortable, exceptionally clean, and peaceful space. We remarked several times while there that it was very enjoyable and that it would be a find place to return in the future.

Carriage House near Navy Stadium, parking, pets
We had an amazing stay at this property! The space was exactly as described. Ingrid was incredibly responsive and thoughtful, providing clear instructions and great local recommendations. The location was perfectâquiet, safe, and close to everything we needed. Weâd absolutely stay here again and highly recommend it to anyone looking for a hassle-free and relaxing stay.

Nautical Charm and relaxing waterview!
Pamâs cozy cottage was the perfect birthday getaway from DC. Door to door was 45 minutes. The view of the Rhode River was so serene and relaxing. I loved watching the chickens, and they were quiet as a church mouse. I was expecting daily morning wake-up calls, but not a peep. The porch was my morning and evening go-to spot for coffee and wine. There are several great restaurants nearby, which I frequented. I asked for a recommendation for a spa and Pam came through. It was the perfect ending to my weekend. I look forward to returning soon. Thank you, Pam!

The Studio on the Severn (Waterfront)
My boyfriend and I stayed here for a wedding and fell in love with the view of the Severn River. It is so peaceful and quiet. It was a wonderful getaway within driving distance of downtown Annapolis. We hope to visit and stay again.

Private Severn Riverfront Guest Cottage
Lisa and Jim's place was absolutely stunning. The neighborhood is so beautiful and the property itself is so darling. We loved seeing the garden and the honey bees hard at work, the flowers were so pretty, so many butterflies and other pollinators! I wish we had had more time to take a few morning walks, because the area is perfect for it. Lisa and Jim are so friendly, and even provided us with a sample of their honey! The space itself is beautiful, clean, we had plenty of extra linens, towels, even toiletries, the kitchen was fully stocked, plenty of entertainment, and the hosts did a great job of recommending lots of local places. Highly recommend!
Guest house rentals with a patio

Magnolia Cottage-BlueHeronLandng
My Husband and I had a wonderful stay at Magnolia Cottage! Blue Heron Landing is beyond words. Liz was so accommodating in every way possible. Thank you for sharing such an amazing place, you get to call home! We will definitely return!

Eastport Coastal Cottage - Patio - Walk Downtown!
Connor and Abigailâs place was absolutely perfect for our week! It was so quiet, clean, and comfortable and had everything we needed. The neighborhood is super cute and so close to all the shops in downtown Annapolis. Itâs also a pretty central location for visiting DC and Baltimore as well. I would absolutely stay here again!

Riverview Retreat on Warehouse Creek
A beautiful retreat to unwind and relax. The homeowners were friendly and welcoming. They've done a lovely job making the place inviting and easy to feel at home right away. We loved it! There is a little bit of noise when kids are over and are running around the house over your head, but I think that is mostly a Sunday family gathering, and it didn't last too long. I would definitely stay here again!

Adorable 1 BR guest house with water views, deck
I loved staying at this wonderful Airbnb! It is just perfect for a single or a couple. On the water, in a quiet setting, just outside Annapolis. Clean, beautifully decorated, very comfortable bed and a great shower and bathroom. Arrived right as a storm was coming and the host met me and helped me get into the unit quickly just as the storm hit (very appreciative!). Set up my work laptop- internet was great. Not a work trip but somehow work usually needs a bit of attention. I can't say enough about how perfect this was for me. The water view front and back was lovely. I sat on the back deck with my coffee and just soaked up the sun. It was so comfortable and I hope to be back to visit again. Thank you!

Modern Sunnyfield Guesthouse
Kiwi was super accommodating and nice. Always responsive and helpful. Really really like the property as well. Itâs beautiful and well taken care of she was very generous with all of her outside space. Enjoyed!

Guesthouse on The Weems Creek
Wonderful escape in Annapolis! Private, clean, and peaceful. Host was very responsive and helpful. The guest house was fantastic and really helped us to unwind. Would definitely stay again!

"The Perch" - Tiny 1BR Cottage - Chesapeake Bay
Paul was a great host. He contacted us personally before check in to make sure we were all set and knew everything we needed to know. He also made a great restaurant recommendation (Boatyard Bar and Grill). The place itself was fine. The bed was very comfortable, everything worked very well. There was both a drip and Kuerig coffee maker, which I personally loved! There was a nice water cooler in addition to the tap water. It is in a very pretty quiet area on the bay, a bit of a drive from the action in Eastbay and Annapolis (about 5 miles). My two recommendations to anyone staying there is that the air-conditioning unit works very well, but can blow directly on the occupants. If you manually push up the vent flaps the air stream will be redirected upward and away from you. The shower runs of hot water in a few minutes (5-10 minutes) so be quick!
Guest house rentals with a washing machine and dryer

Charming Guest House-Annapolis
Marvelous place, we had a great time for a reunion weekend. Definitely recommended, super taste for decoration and details.

Eastport Gem ~ Walk to Downtown Annapolis
This place is absolutely perfect. It looks straight out of a coastal living magazine. VERY clean, new furniture, beautifully decorated in a Navy theme and it has everything you could possibly need. Hosts were so welcoming. The location was an easy 10 min walk (or less) to the heart of Annapolis. If you want to feel like you are staying in a 5star hotel with all the amenities of a home, stay at Kathleenâs. We will be back and will recommend to friends!

New spacious private guest suite
Charles was very friendly and helpful! His place was very well kept, private, and peaceful. I felt at home the entire stay! The cost was extremely reasonable. I would definitely stay again.

Magothy River Bay Cottage
Very cute, light filled, spacious, and tastefully decorated, above garage apartment with a beautiful water view. The furnishing and appliances are upscale (the reverse osmosis water filter is a nice pulse), the bedroom is spacious, with a comfy bed, and walk in closet. You have a Smart T.V. and desk to work remotely in living area. Having a designated parking spot right by the front door is convenient. The neighborhood is quiet, walk/bike friendly and has several very nice waterfront parks. There is a shopping center approximately 5 minutes away that has a coffee shop, good restaurants, grocery, and pharmacy. Robert and June are responsive and accommodating hosts. Thanks for sharing your lovely home!

Peaceful estate retreat Near DC National Harbor
We enjoyed our stay at the Gittens home! Everything was just as expected! We would love to stay there again. We recommend that the tvâs all be upgraded to smart tvâs in order to stream movies. Also it wouldâve been great to have full access to the pool. Humberto said that he is going to get pool access covered with Airbnb. It may be necessary to include the proper insurance coverage with Airbnb to allow coverage for the pool and hot tub. I recommend that until you have the coverage donât include the pictures of the pool area because it can be misleading to potential residents. My overall experience was great! Thank you to the Gittens family for welcoming us and making our stay very enjoyable! You wonât find nicer hosts!!
Destinations to explore
- Rentals with lake access Anne Arundel County
- Flat rentals Anne Arundel County
- Waterfront rentals Anne Arundel County
- Rentals with breakfast Anne Arundel County
- Rentals with a hot tub Anne Arundel County
- Rentals with a patio Anne Arundel County
- Rentals with beach access Anne Arundel County
- Beachfront rentals Anne Arundel County
- House rentals Anne Arundel County
- Fitness-friendly rentals Anne Arundel County
- Private suite rentals Anne Arundel County
- Rentals with a kayak Anne Arundel County
- Family-friendly rentals Anne Arundel County
- Rentals with a washing machine and dryer Anne Arundel County
- Family-friendly rentals Anne Arundel County
- Rentals with a firepit Anne Arundel County
- Rentals with pools Anne Arundel County
- Townhouse rentals Anne Arundel County
- Rentals with a fireplace Anne Arundel County
- Rentals with outdoor seating Anne Arundel County
- Pet-friendly rentals Anne Arundel County
- Apartment rentals Anne Arundel County
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Georgetown Waterfront Park
- Patterson Park
- Arlington National Cemetery
- Washington Monument
- Great Falls Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD
- Meridian Hill Park