Guesthouse holiday rentals in Maryland

Maia’s Cozy Cottage is perfect. It is appointed with whatever you need; microwave, hot plate, coffee maker, air fryer, fridge, basic kitchen utensils, dinnerware, cooking & light cleaning essentials. She even has a refillable water filter in the fridge. The bathroom has plenty of towels (makeup removal towels, too!) & basic essentials like shampoo, lotion, Q-tips, hair dryer, etc. The cottage itself was lovely. It was such a comfortable, clean place to stay in for the week. It has two separate AC remotes, a tv in the bedroom, nice walk in closet, books, a few games & a lovely living area. I brought my 16 year old son to OC with me & he could not say enough nice things about this place. He especially loved the hammock, fish pond out back & said the bed was super comfy. Maia was very responsive to messages & checked in on us a couple of times throughout our stay. She had a handy list of nearby shops, restaurants & activities. I will definitely rent this place out again. Loved our stay

Everything was great in this apartment! It was cute and clean with all the necessary amenities. Roland was quickly responsive when my dad locked himself out and helped us get in with no problem. Thank you.

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.

Felt like a home-away-from-home! So much more than a hotel room. Very peaceful area with a very good view. Bed was comfortable. It was obvious that Pam cares about her clients I will be recommending this to others.

This is a beautiful, private place with amazing nature. We saw deer and hummingbirds, and they were pretty close to us. This place has a wonderful cat (Mr. Moo) who will give you much love! It is a bummer that we didn’t see dogs, but we got to see the chickens and got eggs from them! Amazing place! Although we may not hear beautiful sounds like others mentioned, we felt the peace and mindless presence. We enjoyed our time, and it was a perfect place for our short retreat.

Will’s place was great! The perfect spot for a getaway for 2. We loved it and will look forward to our next visit! Thanks Will!

The lovely “cottage” on Deb‘s property was gorgeous, serene & just what the dr ordered for this exhausted DC mom! Deb couldn’t have been more welcoming; provided an amazing spread of fresh fruits, cookies, a lemon cake, wine, bagels w/cream cheese & OJ in the fridge. Super appreciated as we didn’t arrive until 9:30PM the 1st night. The 1st few days, my teen son & I enjoyed the tranquility of the property, including the refreshing pool & plenty of fun activities nearby. Then, my husband (who had to work), picked up our son so I cld decompress & have a couple much-needed days to hang out w/girlfriends who joined me @ the cottage. Although our last full day was a tad rainy, it didn’t deter us from having a delish brunch in town, checking out the arts festival by the canal & stepping into some cool stores on the main st of vibrant Frederick. Deb‘s accommodations were uber-plush; by far the most luxurious AirBnB I’ve ever stayed in. Thank you so much for the cathartic reset, Deb! 😮‍💨

We really enjoyed the caretaker's cottage located within minutes of our family gathering nearby. We appreciate the efforts made by John and Fiona to retain the historic authenticity and charm of the property while adding some 21st century amenities. The only regret is that we did not accept the offer of fresh eggs from their henhouse. Perhaps next time...

We rented both the main house and the cabin for our large group which provided us a ton of space for our large group of adults. Lukas was responsive and helpful, accommodating a late check out when our schedule changed due to the weather. The location is beautiful and from the minute we stepped out of the car we were relaxed. The house and cabin were clean and well thought out. The river is amazing and you see it from almost every window. The covered outdoor areas made our day of rain nothing to worry about. Would definitely go back and recommend to others!!

We enjoyed our stay at the loft. Linda was very helpful and responsive when we had a few minor issues/questions during our first day check in. You could tell Linda put a lot of thought into ensuring guests had all the amenities needed for a comfortable stay. We had everything we needed for a comfortable stay. The A/C thermostat and some of the light/fan switches were located downstairs which was a minor annoyance if you need to make frequent adjustments. This was not a big concern for us, just something to note for those who have limited mobility going up and down stairs. Overall we had a great stay and would recommend it to others.

The bed is probably the most important thing for us when choosing a rental. The master bedroom bed was excellent. The second bedroom, not so much. But if you don’t have back issues, it’s ok. We are really bed snobs 🥺

Perfect spot for visiting family in the area. Immaculately clean, cozy, all the amenities we could need, and super comfortable beds. Katelyn was such a warm and gracious host - we appreciated the special local touches (delicious cider donuts) and her incredibly kind hospitality. The pool was perfect and we thoroughly enjoyed it. We truly couldn't have hoped for a more wonderful stay and hope to return again! Our many thanks for an ideal stay!

Megan's Sunny Guesthouse has become our home away from home when we go to Baltimore to visit our grand kids. It is a spacious room over a garage that was once an office. Has a small kitchenette, small desk, sofa, TV and table for eating and a nice shower. In addition, Megan is a very responsive host. Great find.

5 stars for sure! The detached garage was even nicer than the photos! The neighborhood was so peaceful and had coffee just a short walk away. Rams Head on Stage was a blast of a concert venue too! Thanks Jocelyn for the awesome stay, pets, and local recommendations :) I would absolutely stay here again and strongly recommend

Amazing place to stay it’s clean, easy to book, affordable, and nice people.

Beautiful and comfortable apartment and great location to Assateague island and other local hiking spots. Wendie was a great communicator. We had a great stay and would love to come back in the future.

Donald's place was great! Even better than advertised. We were a party of 5 attending an Annapolis graduation, and we couldn't have been more satisfied. Our hosts Donald and Julie were fantastic! Its a quiet, peaceful neighborhood with free beach. We highly recommend it!

Pure praise for Amanda and what she has done with the space. It’s exactly as described, very clean. Attention to detail with labels and well thought out amenities . I will definitely return.

Another peaceful stay at Drayton farm. Ken and Leanne are the best hosts.

This place is one I would definitely come back to. The design of this place is absolutely gorgeous! Clean and the host was always responsive when needed. This place is very close to DC which was our goal since we had an event close by. Certainly would come back again! It’s also close by to quite a few grocery stores, so if you need anything. You can come pick it up nearby. Things like Whole Foods, CVS, and more

Had a wonderful stay, is a very clean and comfortable unit. Had all essentials, was quiet and in a very safe area. Can walk to the brewery, and really enjoyed relaxing on the deck. Great instructions and photos made it easy to access unit. Will definitely stay here again

This was by far my most pleasurable stay I have ever had booking with airbnb. The host was friendly, responsive, and ensured that anything we could ask for was available. I would 100% recommend others to stay here. From the moment we walked in it felt like a true home. The furnishings we cozy and the aesthetic was far above the average. It felt like a fancy hotel stay. I would have loved to stay for a month or even rent from this owner 😅

My friend and I stayed at Joelle's place and we loved how cozy and big enough for the two of us. We did have some friends and family come over as well, and it was able to fit us all. The kitchen had everything we needed and the beds were so nice to sleep on.

Candace was an excellent and thoughtful host. She offered great recommendations to help us explore the community. Our stay was peaceful and restful. The property feels suburban or even rural despite being in the city and just minutes from the interstate. We often saw dear, rabbits, and foxes in the woods beside the cottage. Great experience!