
House holiday rentals in Hollywood, St. Mary's County
Find and book unique houses on Airbnb
Top-rated house rentals in Hollywood, St. Mary's County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Hollywood, St. Mary's County
House rentals with a pool

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks
Andrea was so responsive from day 1 when I had questions about the house! We had 10 people in town for a wedding and her house was only 3 miles from the venue which was ideal! The house was clean and had nice little extra touches; the bottom floor was surprisingly spacious and perfect for hanging out! And the hot tub was a nice add also! Overall, it was a great experience!

Gorgeous, waterfront home - Perfect for Families.
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Spacious and private waterfront, sleeps 10
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

Beach Please! River cottage w/private beach & dock
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.

Family Friendly: Hot Tub, Grill, Pool & More!
This was one of the most well equipped houses I have ever stayed in. The hosts were very easy to communicate with and responded quickly to each contact. I highly recommend this place!!

5 BEDR, Inground Pool+Billiard Table, Close To D.C
Daniel’s Home was beautiful and he made this special event for me and my family able to celebrate my sons 26th Heavenly Birthday a success We were very comfortable and it really felt like home the pool was very clean and the Home was very spacious and squeaky clean I would love to Book Daniel again He was a very nice and friendly Host that responded to any questions we had he made communication easy me and my family really enjoyed our self and yes he’s reasonable and you definitely get what you paid for and more Thank you again Daniel

Brigadoon, the BRAND NEW Waterfront Haven
This house was perfect for our family mini vacation. The view was incredible, the house was stocked with all sorts of thoughtful extra touches. We loved the kayaks, paddle boards, tubes and beach area. Pam was so helpful and responsive. Everyone had a great time!
Weekly house rentals

Large home w/ 6 bedrooms, 2 kitchens, and hot tub!
It was a great place to stay for a mini-family gathering! Shelly even provided a booklet with local restaurants and activities in the area.

Beautiful, serene waterfront property
An incredible peace of property! This house has been beautifully renovated and exceeded every expectation. Unbelievable waterfront views from nearly every room in the house, back porch and fire pit. Also a very nice surprise of having a little play area stocked with toys for the little ones! This is a must stay if we’re ever back in the area!

Chesapeake Escape
We had a great stay! The place was really clean and had great views of the beach.

Potomac River Getaway
Had a great weekend in the Northern Neck here! We watched a pod of dolphins and stingrays from the backyard, enjoyed easy access to nearby parks, and had a great time cooking in the kitchen. This is seemingly a very recently renovated house, and all the towels, sheets, beds, etc. seemed brand new as well. It was super clean, super comfy, and the hosts were very responsive! I liked that the property was surrounded on one side by forest as well—it was nice and quiet and secluded. Finally, they have a super cute collection of board games disguised as old timey books. I'd definitely stay here again!

Waterfront! The River's Roost on the Patuxent!
My wife, 4 year old son and I enjoyed a week at John’s beautiful home on the Patuxent River. The house and property were perfect and the views were amazing every day. The house had everything we needed and we felt right at home. He was very responsive and helpful when we had questions. We look forward to staying here again in the summer!

Solomons home with harbor view!
This was our first visit to Solomon’s Island and the location of this home was perfect. Mother uses a rollator for walking and could easily walk from the house to the boardwalk daily. We spent many hours on the second floor covered deck enjoying the activity at the harbor. Terri gave us good upfront information to help us prepare for our stay. The home was clean, quiet, and comfortable.

2 Bedroom Cozy Beach Cottage
Michelle is a great host. The place is clean and has many conveniences. I highly recommend!

Riverview Retreat
This served as a low key weekend retreat for us. We unplugged and enjoyed being in each other’s company. Being on the river, surrounded by trees and birdwatching was exactly what we needed. The kitchen was well appointed so we were able to enjoy family favorite activities (cooking together and playing board games).
Private house rentals

Solomons Yellow House - Waterfront
Came to Solomon’s for a wedding . Had a wonderful stay at John’s Place. All the comforts of home. Very clean, Fantastic location- easy walk to restaurant’s, shops, And Mass on Sunday ! Beautful water front property. Lovely decor- excellent kitchen space. Lovely the unique lighting, screened -in porch, and front porch! Very Comfy beds. Would def stay here again!!

Stunning Views, Remodeled Family-Friendly Home
This was a truly lovely and clean home. Staying there was so wonderful - sitting on the screened porch listening to the water, walking the waterfront, lovely. It was so peaceful and calming of a location. Also, walking or biking distance to the St. Marys college and historical park. I recommend anyone stay there - I would again. We felt so comfortable and welcomed into this gorgeous waterfront property. You cannot beat the views and location. Communicative hosts. Thanks for a great stay!

Coastal Haven- Beach w/ BBQ
My family had a wonderful stay at this BNB. Lots of space for everyone. Big rooms, really nice kitchen. It was very neat and clean. The neighborhood access to the beach was a plus. The neighborhood is very nice and convenient to the highway.

Waterfront home with three bedrooms,3 full baths
Really great place with all the amenities of home!

Waterfront home, private dock
We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.

Luxury Modern Waterfront Retreat
Kelly and Thomas were amazing host. Very responsive and accommodating The home was very clean and the location was great.. 10/10. Definitely would book again!

Rivah view get away
We were in the area to explore George Washington’s Birthplace and Stratford hall and had a lovely stay at Susan’s place. The beds were comfortable, we cooked and sat on the front porch listening to the rain. The tavern is within walking distance but we didn’t get a chance to go. Hoping to come back again because the area is fabulous!

SoMD Waffle House 1.5 acres of cozy coastal living
We really enjoyed our stay here. It was relaxing and super chill.
Quick stats about house rentals in Hollywood, St. Mary's County
Total rentals
30 properties
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Nationals Park
- The White House
- National Mall
- Georgetown University
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Quiet Waters Park
- Lee's Hill Golfers' Club
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Library of Congress
- Gerry Boyle Park
- American African Museum
- Ragged Point Beach