Guesthouse holiday rentals in Anne Arundel County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Anne Arundel County guesthouses

Family-Friendly guesthouses

Guesthouse in Annapolis
4.88 out of 5 average rating, 197 reviews

Annapolis Guesthouse - Completely Separate Space

KirkRating, 5 stars1 week ago
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.
Top Guest favourite
Guesthouse in Annapolis
4.94 out of 5 average rating, 106 reviews

Carriage House near Navy Stadium, parking, pets

RobertRating, 5 stars3 weeks ago
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 perfect—quiet, safe, and close to everything we needed. We’d absolutely stay here again and highly recommend it to anyone looking for a hassle-free and relaxing stay.
Guest favourite
Guesthouse in Galesville
4.95 out of 5 average rating, 172 reviews

Nautical Charm and relaxing waterview!

CindyRating, 5 starstoday
Pam’s 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!
Top Guest favourite
Guesthouse in Crownsville
4.98 out of 5 average rating, 66 reviews

The Studio on the Severn (Waterfront)

SarahRating, 5 stars2 weeks ago
This air bnb was a slice of paradise. The view is the water was breathtaking. The hosts left a lovely breakfast bread for us. Everything about this stay felt like a comforting hug. Thank you!
Guest favourite
Guesthouse in Severna Park
4.98 out of 5 average rating, 83 reviews

Private Severn Riverfront Guest Cottage

ValerieRating, 5 stars8 months ago
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!

Guesthouses with a patio

Guesthouse in Stevensville

Magnolia Cottage-BlueHeronLandng

JusmaryRating, 5 stars2 months ago
Everything from start to finish was amazing. This is the true meaning of going above and beyond. Liz was a fantastic host very accommodating, communicative and caring. She made my husbands birthday unforgettable.
Top Guest favourite
Guesthouse in Annapolis
5 out of 5 average rating, 8 reviews

Eastport Coastal Cottage - Patio - Walk Downtown!

TaraRating, 5 stars1 month ago
Conor and Abigail were excellent hosts and we had a wonderful stay. We enjoyed walking to nearby restaurants and downtown Annapolis! The place was decorated beautifully and so clean!
Superhost
Guesthouse in Edgewater
4.85 out of 5 average rating, 20 reviews

Riverview Retreat on Warehouse Creek

ElizabethRating, 5 stars1 month ago
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!
Guest favourite
Guesthouse in Arnold
4.88 out of 5 average rating, 17 reviews

Adorable 1 BR guest house with water views, deck

LaurenRating, 5 stars1 day ago
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!
Guesthouse in Baltimore
4.86 out of 5 average rating, 7 reviews

Modern Sunnyfield Guesthouse

JamieRating, 5 stars7 months ago
Kiwi was super accommodating and nice. Always responsive and helpful. Really really like the property as well. It’s beautiful and well taken care of she was very generous with all of her outside space. Enjoyed!
Top Guest favourite
Guesthouse in Annapolis
5 out of 5 average rating, 30 reviews

Guesthouse on The Weems Creek

ConradRating, 5 stars1 month ago
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!

Guest house rentals with a washing machine and dryer

Guesthouse in Annapolis
4.8 out of 5 average rating, 30 reviews

Charming Guest House-Annapolis

AugustoRating, 5 stars20 months ago
Marvelous place, we had a great time for a reunion weekend. Definitely recommended, super taste for decoration and details.
Top Guest favourite
Guesthouse in Annapolis
5 out of 5 average rating, 27 reviews

Eastport Gem ~ Walk to Downtown Annapolis

JohnRating, 5 stars1 week ago
We had an absolutely beautiful weekend in Eastport. The guest house was meticulously clean and had everything we needed. The hosts were very communicative and hospitable. We walked to restaurants, bakeries, and quaint coffee shops. The guest house was quiet and cozy! The perfect weekend getaway! Can’t wait to return.
Guest favourite
Guesthouse in Hanover
4.96 out of 5 average rating, 26 reviews

New spacious private guest suite

TomRating, 5 stars1 month ago
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.
Top Guest favourite
Guesthouse in Arnold
4.91 out of 5 average rating, 23 reviews

Magothy River Bay Cottage

MaryRating, 5 stars10 months ago
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!
Superhost
Guesthouse in Upper Marlboro
4.82 out of 5 average rating, 11 reviews

Peaceful estate retreat Near DC National Harbor

MichaelRating, 5 stars9 months ago
We enjoyed our stay at the Gittens home! Everything was just as expected! We would love to stay there again. We recommend that the tv’s all be upgraded to smart tv’s in order to stream movies. Also it would’ve 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 don’t 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 won’t find nicer hosts!!

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