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Guest house holiday rentals in Southern Maryland

Find and book unique guest house rentals on Airbnb

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Popular amenities for guest house rentals in Southern Maryland

Family-friendly guest house rentals

Top guest favourite
Guest house 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.
Top guest favourite
Guest house 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!
Top guest favourite
Guest house in Manassas
4.93 out of 5 average rating, 100 reviews

Private Luxury Retreat Close to everything!

OscarRating, 5 stars1 week ago
We had a great stay! Check in instructions were clear and the space was clean and well-kept. Check out was a breeze as well. Monica was always responsive and friendly.
Superhost
Guest house in Herndon
4.76 out of 5 average rating, 220 reviews

Historic Herndon In-law house, kitchen. By IAD.

Mary BernadetteRating, 5 stars1 month ago
Very beautiful Airbnb !!! Private and very quiet neighborhood , everything we needed was in the unit down to the Keurig pods , extra perk for the rice cooker and Instapot. The bed was spacious and very comfortable It was like being in our own oasis Lots of memorable moments and will always cherish our time there Check out as a breeze and will definitely come back again if we need another get away
Guest favourite
Guest house in Glen Allen
4.84 out of 5 average rating, 563 reviews

Private and Quiet Pool House Convenient Location

CarlosRating, 5 stars1 week ago
Teenagers point of view...easy, chill, and very comfortable. Loved the pool time (2 teenage girls) From an adults point of view... loved the privacy, pool by the room. It was very relaxing and pleasant. Exactly what we needed for the weekend. We also loved the pool. Owner was very pleasant and quick to respond. We will book again.
Superhost
Guest house in Oxford
4.83 out of 5 average rating, 134 reviews

Bonfield Bungalow

StaceyRating, 5 stars3 weeks ago
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!
Guest favourite
Guest house in Washington
4.86 out of 5 average rating, 364 reviews

Historic Carriage House + Parking!

JoeyRating, 5 stars2 weeks ago
Absolutely loved the carriage house, it was exactly what i expected and I’d 100% stay there again. The location was perfect and having a parking spot was so convenient. We didn’t cook or anything so i can’t review much on that but everything we would’ve needed was there if we had. Loved the security of the locked gate and the bed and linens were so so comfy, it was hard to get out of bed it was that comfortable. I’ll definitely stay again when I’m back in town.
Top guest favourite
Guest house in Ashland
4.95 out of 5 average rating, 565 reviews

2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi

MarianaRating, 5 stars3 weeks ago
It’s always great to stay at the cottage. Beautiful surroundings, clean and comfortable place with consistently unexpected details

Guest house rentals with a patio

Top guest favourite
Guest house in Ridge
4.93 out of 5 average rating, 46 reviews

El Camino

JenniferRating, 5 stars1 month ago
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!!
Top guest favourite
Guest house in Washington
4.95 out of 5 average rating, 213 reviews

GardenLevel 4BR/2.5BA-Parking+By Convention Center

MariellaRating, 5 stars2 weeks ago
Alma’s place was fully renovated, beautiful finishes, gorgeous floors, super comfortable beds and impecable bathrooms. Kitchen was modern and had everything needed for cooking. Excellent location and walking distance grocery store. Alma was friendly and promptly answer all of our questions. She also allowed us to leave our luggage before check in time. We had a wonderful time and will be back for sure!
Guest favourite
Guest house in Lorton
4.94 out of 5 average rating, 49 reviews

Villa Miza Wellness Retreat

BesanRating, 5 stars1 month ago
The guesthouse was super cute and cozy. Everything was very clean and organized. The location and neighborhood made me feel safe and comfortable so I liked that. Michele was also very helpful and responsive so that was very nice! There were also lots of restaurants around the area going from 4-10 minute drives! Overall I very much enjoyed my stay and would absolutely come back again!
Top guest favourite
Guest house in Washington
4.98 out of 5 average rating, 238 reviews

Gorgeous Two-Story Guesthouse w/ Driveway & W/D

JulienRating, 5 stars1 week ago
very nice, clean, spacious and convenient place. we enjoyed staying there very much and would consider staying there again next time we visit DC
Guest favourite
Guest house in Washington
4.96 out of 5 average rating, 107 reviews

DC Treehouse - Charming, private 1-bdrm ADU in DC

DeniseRating, 5 stars4 weeks ago
My husband and I had a delightful stay at Chris Zarconi's Airbnb. We were in town for our son's graduation, and having this lovely place to come home to in-between events, was very comforting and peaceful. I enjoyed morning coffee listening to the birds outside the sliding door. The neighborhood was lovely and I was able to walk each morning. I would definitely come again should I need a place to stay in DC.
Guest favourite
Guest house in Washington
4.88 out of 5 average rating, 245 reviews

Adorable English Basement on 15th St

AlexRating, 5 stars1 week ago
Enjoyed a great stay here during World Pride! Very walkable to the Metro. Felt safe walking around late at night. Space was clean with a very comfortable bed. Would definitely recommend!
Guest favourite
Guest house in Alexandria
4.91 out of 5 average rating, 146 reviews

The Guest Suite

KyleRating, 5 stars6 days ago
Very comfortable stay! Grateful for the dog friendly accommodations while in town for a wedding. The suite was well equipped and nice to have a kitchen for light meal prep. Convenient location with Uber for wedding events. Lindsey was very responsive and friendly. Would stay here again!
Top guest favourite
Guest house in Edgewater
4.98 out of 5 average rating, 116 reviews

1 large room efficiency in detached garage.

ThomasRating, 5 stars1 week ago
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

Guest house rentals with a washing machine and dryer

Guest favourite
Guest house in Annapolis
4.91 out of 5 average rating, 107 reviews

Private Cottage on gated estate

JhonaRating, 5 stars1 month ago
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!
Guest favourite
Guest house in Washington
4.91 out of 5 average rating, 186 reviews

1.5 blocks to Metro-Guest House-Walk to it all!

AbbyRating, 5 stars6 days ago
The home was comfortable, easily accessible and great for the price. host was incredibly friendly and responsive and was willing to help with anything. Will definitely rent this home again if we're in the area
Top guest favourite
Guest house in Washington
4.99 out of 5 average rating, 113 reviews

Luxurious 1Bed Carriage House, 1.5 Blocks to Metro

RayaRating, 5 stars9 months ago
Our stay in DC could not have been more enjoyable. Everything was clean, thought out, and the location is ideal. The space is curated to be simple yet have everything you may need or want. Just close enough to the national mall for a quick bike ride. And private enough for low noise and safety. The recommendations from Chris were appreciated. Our host was very responsive. 10 out of 10, would book again.
Top guest favourite
Guest house in Arlington
4.96 out of 5 average rating, 192 reviews

Spacious Guest House 10-15 min to DC

AbbieRating, 5 stars2 weeks ago
Absolutely loved staying here, I thought my little would appreciate the loft and he sure did. He was obsessed hanging out in there 😂 it was adorable. It was only about 15 to get to the capital and we went bright and early to beat the crowds and then hung out the early afternoon to the night it was amazing! Instructions covered everything, just be sure to read 🤣 Honestly I used to manage str’s so I will say I can be rather flexible especially if something does come up that I know to be a common issue or just a super like specific/ independent opinion. But literally nothing came up(: Great stay! Would 100000% come back if I needed a place in the area!
Guest favourite
Guest house in Washington
4.96 out of 5 average rating, 192 reviews

Garden Suite

EllenRating, 5 stars1 week ago
Farida’s garden suite was an urban oasis! It’s in a gorgeous neighborhood on a coveted street in DC, equidistant between two avenues that have grocery stores, restaurants, coffee shops, the metro - basically everything you need within a 1/2 mile. Farida was very friendly, communicative, and hospitable, and she addressed any and all of my questions promptly. The suite is charming, the bed is very comfortable, and the space is light-filled and quiet. I loved my stay and hope to return soon!
Guest favourite
Guest house in Alexandria
4.97 out of 5 average rating, 102 reviews

NoVA guest house

MatthewRating, 5 stars1 month ago
Christine was an outstanding host to me - and very responsive (and was very flexible). The air conditioning in my condo building is currently getting repaired. She permitted early check-in, which I really appreciated - and even gave me the opportunity for late checkout. The property has everything you need for an excellent stay - outstanding amenities (you pretty much not need anything when you stay here). I slept so well at their property. This property would be an excellent choice for those who wish to say long-term (like a month or more). You can tell that Christine cares about this property as it is maintained very well. Keep up the great work, Christine.
Guest favourite
Guest house in Annapolis
4.86 out of 5 average rating, 101 reviews

Chesapeake Bay Escape | Cozy Retreat

JacquelineRating, 5 stars1 month ago
We loved our weekend stay at Melanie’s place!! It was clean, easy to access and a lovely location!! She was super helpful with our questions about the areas and places she recommended. Definitely recommend!!
Guest favourite
Guest house in Alexandria
4.93 out of 5 average rating, 126 reviews

Washington Family Historic Property~Upper Studio

LindaRating, 5 stars1 month ago
We enjoyed the historic charm of the Carriage House and LOVED that we were on King Street within seconds. The parking garage was right down the alleyway - with a reasonable overnight rate. We were able to leave it there all weekend while we walked everywhere.

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