House holiday rentals in Shady Side

Find and book unique houses on Airbnb

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Popular amenities for Shady Side house rentals

House rentals with a pool

Guest favourite
Home in Edgewater
4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

NancyRating, 5 stars3 weeks ago
Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.
Superhost
Home in Queenstown
4.81 out of 5 average rating, 156 reviews

Bay Breeze Retreat

EeshaniRating, 5 stars8 months ago
Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.
Guest favourite
Home in Rock Hall
4.95 out of 5 average rating, 37 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 week ago
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"
Guest favourite
Home in Cambridge
4.96 out of 5 average rating, 112 reviews

Gorgeous, waterfront home - Perfect for Families.

Leslie RogersRating, 5 stars5 months ago
We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!
Top Guest favourite
Home in Edgewater
4.98 out of 5 average rating, 53 reviews

Entire Beach House with Pool and Hot Tub

DianeRating, 5 stars5 months ago
We had a great stay at this clean, comfortable, convenient and cozy house. We were impressed by the attention to detail. Every time we needed something, it was there. The kitchen was fully stocked and had everything we needed to cook our Thanksgiving meal. We were close to Annapolis And had an easy drive to the museums of DC. We took several walks to the nearby beach, and enjoyed both sunrises and sunsets. We would definitely come back! Thank you, Peggy!
Guest favourite
Home in Severn
4.88 out of 5 average rating, 164 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

LoisRating, 5 stars1 week ago
Staying here made our family wedding stay away from home, a very memorable and fun weekend for the whole family. Muvh better than being stuck in a hotel with lots of kids!!
Guest favourite
Home in Fort Washington
4.91 out of 5 average rating, 150 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

CurtRating, 5 stars2 days ago
Simple, clean and well organized place .. would definitely recommend.
Top Guest favourite
Home in Tracys Landing
4.99 out of 5 average rating, 207 reviews

The Little Gypsy BoHome

LaurenRating, 5 stars1 week ago
I can’t say enough wonderful things about Melissa’s place. As soon as you walk in, you feel right at home. She has thought of every possible thing you could need while there. The views were absolutely magnificent and while the beach area is available to the public, it felt super private. My daughters and I plan to come here every year. I had to peel them away from the bay. Melissa, thank you for accommodating us. This was a weekend my girls and I desperate needed and your home was the perfect place to have peace and intentional quality time. Thank you so much!!

Weekly house rentals

Guest favourite
Home in Capitol Hill
4.95 out of 5 average rating, 188 reviews

Beautiful Capitol Hill Row House

Mary FranRating, 5 stars2 weeks ago
Maggie’s house was perfect for our family getaway! You can’t beat this location. It was a quick walk to Eastern Market metro and tons of local shopping/dining options, yet the street was peaceful and quiet. We were able to spread out and relax as a family of three with two dogs. The house was comfortable and had everything we needed. Maggie was responsive and helpful from booking and through our stay. 10/10, would book again.
Guest favourite
Home in Arlington
4.83 out of 5 average rating, 12 reviews

Wonderful DC 2-miles away-Parking-Super Convenient

RhondaRating, 5 stars1 month ago
Robert's place is comfortable and clean. The mattresses are comfortable - firm with a soft top. He is friendly, responsive, and full of information about the area. We felt completely at home. It is the perfect distance from the mall. We took an Uber into the city each day and this was an easy, quick, and inexpensive ride.
Superhost
Home in Upper Marlboro
4.83 out of 5 average rating, 6 reviews

Beautiful spacious 4-bedroom home w/2-story lounge

BryanRating, 5 stars3 weeks ago
Nice place, had an issue with the ac but they had issues resolved quickly.
Guest favourite
Home in Dumfries
4.7 out of 5 average rating, 118 reviews

Private Basement/Apartment with Separate Entry

JessicaRating, 5 stars3 weeks ago
Quiet neighborhood, beautiful area. It's in a community, not close to restaurant's or activities. It's a great place to relax at night. Beds were comfy, great shower and kitchen area. Very spacious. Truly appreciated the accommodations on our late check in Can hear the family upstairs as mentioned but Hashim and family were quick to quiet down the kids in the morning, so not a problem. Would happily stay here again.
Superhost
Home in College Park
4.83 out of 5 average rating, 179 reviews

Spacious relaxing home by DC, CP, woods & lake

KarenRating, 5 stars3 weeks ago
Such a lovely, comfortable home. Everything we needed. Loved the location. The neighborhood was extremely quiet and neighbors were friendly. There's a park with walking trails and lake half a mile walk away. The house was perfect. Relaxing. Comfortable beds and bedding. The record player was an added bonus, as were the puzzles and board games for the rainy days. Communication was excellent. Answered any questions quickly and was very helpful. Would definitely stay here again.
Guest favourite
Home in Deale
4.98 out of 5 average rating, 106 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

CarolRating, 5 stars2 weeks ago
Our family had a great time - the property was spacious and clean, location was beautiful, and we loved playing outdoors in the open space and getting out on the water. Hosts were very responsive and everything we might need/want was provided!
Top Guest favourite
Home in Arlington
4.98 out of 5 average rating, 156 reviews

Barcroft House - large yard w/playground near DC

AmberRating, 5 stars8 months ago
Felt like home. Quiet neighborhood with walking distance grocery store. Extra amenities. Very clean and I’m a clean freak.
Guest favourite
Home in Suitland
4.88 out of 5 average rating, 16 reviews

Spacious 7BR/5BA Retreat: 15 mins to National Mall

KimberlyRating, 5 stars1 month ago
⭐️⭐️⭐️⭐️⭐️ Absolutely Perfect Stay! Our stay at Suitlamd Manor, was nothing short of amazing! From the moment we arrived, everything was spotless, well-organized, and exactly as described. The attention to detail—from the cozy decor to the thoughtful amenities—made us feel right at home. The location was perfect, close to everything we needed. yet still peaceful and quiet for a restful stay. Meka was an exceptional host, always responsive and helpful with local recommendations. We truly appreciated the little extras, like complimentary coffee and wine. The bed was incredibly comfortable, and we had everything we needed for a relaxing getaway. I highly recommend this place to anyone

Private house rentals

Superhost
Home in Fort Washington
4.82 out of 5 average rating, 106 reviews

Home away from home near MGM-3bed2bath

FrankieRating, 5 stars3 weeks ago
The space was exactly as described! Very clean and host was very proactive with check in and out instructions. Had a great time visiting the area. Would absolutely stay here again! **to note: there is a resident who lives downstairs, which is noted in the Airbnb description. You can hear them when they enter/exit the home. This did not bother us at all and we were aware of this as it was in the description but I wanted to highlight that for any perspective guests.
Top Guest favourite
Home in Arlington
4.97 out of 5 average rating, 100 reviews

Entire family size house steps to ANC & metro walk

Mary EllenRating, 5 stars1 month ago
Tyler's place was perfect for our stay with our extended family. It's spacious and comfortable, with plenty of room to relax indoors and out. It has a very nice large porch and deck, great for some solitude or for kids to play. The beds were comfy and the linens ample, there are gorgeous large bathrooms and luxurious showers, the kitchen was well-stocked and included an amazing high-end stove, and the living spaces are nicely decorated and furnished with art and tons of books. One bedroom had lots of toys and kids' books, a very nice touch. Tyler was helpful, accommodating, and responsive. The location is very convenient to Arlington National Cemetery and within walking distance to a Metro stop. Everything about this rental was fantastic--we highly recommend it if you need a lovely space for a large group. Thanks, Tyler!
Top Guest favourite
Home in Cambridge
4.95 out of 5 average rating, 231 reviews

Great Historic Cambridge Home With Parking!

AshleyRating, 5 stars1 month ago
What a gem! My daughters and I loved our week spent here. The home is a true beauty with all the charm of a seaside getaway. All of the amenities truly made it feel like home, and the kitchen is amazing! Everything was streamlined and easy, the host was wonderfully responsive, and the home had such a friendly, warm, relaxing feel to it. It was such a terrific experience through and through, I would highly recommend taking full advantage of this beaut!
Superhost
Home in Annandale
4.79 out of 5 average rating, 135 reviews

Gorgeous Chateau Style Home/Mansion

MadisonRating, 5 stars3 weeks ago
Thank you for the amazing girls trip! We had an absolute blast. The house was just as described and matched all photos! We always felt at home and it was beyond perfect. Will stay again if we come back this way!
Superhost
Home in Centreville
4.63 out of 5 average rating, 92 reviews

Peaceful Acres Guest House (A Nature's Getaway)

AnneRating, 5 stars6 months ago
The house was comfortable, clean and quiet. It was exactly what I was looking for to participate in a nearby competition. There were minor issues that the host addressed quickly and we got back to our vacation. Would stay here again.
Superhost
Home in Pentagon City
4.93 out of 5 average rating, 170 reviews

LA Inspired Glasshouse 4min DC| Hot Tub +Ping Pong

MorganRating, 5 stars3 weeks ago
We had a wonderful time staying at this beautiful home. We were pleasantly surprised at the cleanliness of this home when coming in. The beds were extremely comfortable in all of the bedrooms. Great communication and very kind host! Thank you Franck!
Guest favourite
Home in Pasadena
5 out of 5 average rating, 52 reviews

Waterfront CHeerful 2 with Private home

DavidRating, 5 stars3 weeks ago
The cottage /house was peaceful on the edge of an inlet from the Bay. The patio was lovely. It was chilly so we couldn’t use the kayaks. The kitchen was very well equipped. The dishes, utensils, cookware were quality. The extra cozy blankets were nice. He responded to a request very timely. We enjoyed the stay very much.
Guest favourite
Home in Northwest Washington
4.98 out of 5 average rating, 116 reviews

Charming Bloomingdale Row Home with Deck & Parking

JasonRating, 5 stars1 week ago
My wife, two kids, pup and I all enjoyed our stay at this well appointed and super comfy home. It is in a great location with parking on site and a cute park right out the back door. Walk to lots of cute restaurants, bus and metro easily. The host was super accommodating and easy to get in touch with. Will definitely stay here again if ever in the DC area.

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