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

Superhost
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 176 reviews

Private 1 bedroom house

MichelleRating, 5 stars3 weeks ago
Nice quiet neighborhood, host was very flexible and accommodating
Guesthouse in Annapolis
4.88 out of 5 average rating, 194 reviews

Annapolis Guesthouse - Completely Separate Space

PeteRating, 5 stars2 days ago
Hosts were lovely, incluing their sweet dog! Quiet, clean, with all we needed including coffee.
Guest favourite
Guesthouse in Galesville
4.95 out of 5 average rating, 170 reviews

Nautical Charm and relaxing waterview!

LeeRating, 5 stars5 months ago
I stayed here visiting family nearby. The place is very clean and set up thoughtfully for guests. I really appreciated that it was already stocked with some coffee and creamers, so I didn't need to go shopping right after arriving. The neighborhood is small but walkable and has two good seafood restaurants a short walk away. Pam provided clear instructions and communication.
Top Guest favourite
Guesthouse in Annapolis
4.94 out of 5 average rating, 103 reviews

Carriage House near Navy Stadium, parking, pets

RachelRating, 5 stars1 month ago
Ingrid and Jay were very welcoming - they made us feel like family friends instead of Airbnb guests. The carriage home was charming and decorated nicely. It felt like home for the weekend!
Top Guest favourite
Guesthouse in Crownsville
4.98 out of 5 average rating, 64 reviews

The Studio on the Severn (Waterfront)

MeganRating, 5 stars4 months ago
We were in and out but the cleanliness and privacy of the space were beyond expectations. A perfect little resting spot in Arnold!!
Guest favourite
Guesthouse in Severna Park
4.98 out of 5 average rating, 83 reviews

Private Severn Riverfront Guest Cottage

ValerieRating, 5 stars7 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

Superhost
Guesthouse in Millersville
4.67 out of 5 average rating, 6 reviews

Newly Renovated 2b/1ba Unit

DavidRating, 5 stars10 months ago
Lionel is a good host. He's calm has a great sense of humor. He keeps the lawn and grounds trim and neat. There is plenty of parking. The amenities are as listed in the ad. I had a relaxing stay in the apartment.
Guesthouse in Baltimore
4.86 out of 5 average rating, 7 reviews

Modern Sunnyfield Guesthouse

JamieRating, 5 stars6 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, 22 reviews

Charming Rental in the Heart of Annapolis

LindsayRating, 5 stars2 days ago
Great experience and lovely place. Enjoyed the neighborhood.
Top Guest favourite
Guesthouse in Annapolis
5 out of 5 average rating, 28 reviews

Guesthouse on The Weems Creek

GayleRating, 5 stars4 months ago
This place was just as described and exactly what we needed for the weekend! Lindsey made sure we have sheets and blanket for air mattress as there was 3 of us and even brought an extra mug to make sure we were all taken care of. Place was comfy. Everything was taken care of!
Top Guest favourite
Guesthouse in Annapolis
5 out of 5 average rating, 6 reviews

Eastport Coastal Cottage - Patio - Walk Downtown!

KarenRating, 5 stars3 weeks ago
Conor and his wife accorded us an opportunity to relax and enjoy the most beautiful part of Annapolis - walked on the quiet side of town, enjoyed Oscar's coffee on Eastern Ave., and most importantly the Eilen Jewell show at the Goat'sHead. Would highly recommend to all. These two are special and present a beautiful getaway: clean and restorative - will be back for sure - chris and karen - thank you both
Superhost
Guesthouse in Edgewater
4.84 out of 5 average rating, 19 reviews

Riverview Retreat on Warehouse Creek

NathanRating, 5 stars2 weeks ago
Great location right on the lake. Very special accommodating hosts.
Guest favourite
Guesthouse in Annapolis
4.88 out of 5 average rating, 65 reviews

"The Perch" - Tiny 1BR Cottage - Chesapeake Bay

EllisRating, 5 stars1 month ago
We had a fantastic weekend stay in Annapolis! Paul was proactive and responsive. The Cottage was clean, super cozy. Super walkable neighborhood with water access. Easy drive to everything we wanted to do. Would stay again!

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Annapolis
4.86 out of 5 average rating, 98 reviews

Chesapeake Bay Escape | Cozy Retreat

TracyRating, 5 stars6 days ago
Melanie was a great host and our stay was comfortable. The cottage was clean, cozy and all amenities provided. The beach is just a short walk from the cottage, and shopping and restaurants are plentiful. We enjoyed our stay and highly recommend. Thanks, Melanie!
Guesthouse in Annapolis
4.79 out of 5 average rating, 29 reviews

Charming Guest House-Annapolis

TimothyRating, 5 stars23 months ago
Overall I had a pleasant stay at Christa's "charming Annapolis Guesthouse" rental. There was a small hiccup with the hot water not working initially, but Krista had it taken care of right away for me. She was very responsive throughout the rental process. It's worth mentioning that, despite the listing title, this isn't an actual seperate guest house but rather more of an attached apartment.
Top Guest favourite
Guesthouse in Annapolis
5 out of 5 average rating, 18 reviews

Eastport Gem ~ Walk to Downtown Annapolis

LauraRating, 5 stars1 week ago
We had a fabulous stay at Kathleen's place! The Guest House was super clean and a comfortable place to relax. We loved the design, layout, and furniture of the home. The location is perfect. You can walk to fabulous restaurants, coffee spots, and downtown Annapolis. Parking was super easy. We had a lovely stay!!
Top Guest favourite
Guesthouse in Hanover
5 out of 5 average rating, 23 reviews

New spacious private guest suite

JaydenRating, 5 stars1 month ago
The place was great! Very spacious and clean. The host is also very quick to respond and even allowed me to have visitors for a short time! Only thing that happened was I ran out of toilet paper as there was no extra rolls and had to buy my own. I’m sure the host would’ve let me ask for extras since he is very understanding and sweet. Will be back again!
Top Guest favourite
Guesthouse in Arnold
4.91 out of 5 average rating, 23 reviews

Magothy River Bay Cottage

MaryRating, 5 stars8 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 stars8 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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