Holiday Rentals in Hollywood

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Holiday Rentals in Hollywood

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (171)
"Great time!! Floridians playing in the snow!! Cozy fire afterwards in the fireplace. Picturesque drive up to the Navy Cabin, deer playing in the snow too."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (127)
"This was our mid-Winter get away from the city. The home is cute, quiet, and well appointed. The host is welcoming and responsive. We had a lovely, restful stay. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (75)
"Great house. Had everything you need for a vacation rental. Had great views, watched ducks and eagles. Got sharks teeth from beach. Definitely recommend to ones seeking Bayfront getaway."
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Maryland Vacation Rental w/ Private Pool & Dock

10.0 out of 10, Exceptional, (6)
"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "
Maryland Vacation Rental w/ Private Pool & Dock

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (39)
"We enjoyed a relaxing and rejuvenating time here while we rang in the new year. The home was lovely and the community was friendly."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

The Schultz Estate

8.4 out of 10, Very good, (15)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is €278
includes taxes & fees
20 Feb - 21 Feb
Soul Oasis - home on the Chesapeake Bay

Beach Club: your own private "Caribbean" resort

9.8 out of 10, Exceptional, (9)
"Beautiful home with lots of room for all 11 of us to enjoy meals and hanging out. Great space to accommodate all ages from 4 to 80. Hosts were very responsive and made us feel welcome. The pavilion at the beach was awesome and we spent alot of time there. Great stay , great memories and all had a memorable time. "
Beach Club: your own private "Caribbean" resort

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

10.0 out of 10, Exceptional, (12)
"Myself, my partner, my 7 family members and our 2 pups stayed here for our annual vacation to Colonial Beach & our experience was nothing short of spectacular. The host is super fast at replying, made our check in process easy, and was super hospitable. They even accommodated our last minute wish to check in early! The ONLY thing I can think of that can be improved is the level of cleanliness. Everything was beautiful and clean except for areas underneath the rugs, which were covered with sand...
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (63)
"This was a great stay. Very nice, comfortable, great layout, convenient location. I highly recommend. "
Inviting and Serene Home on Monroe Bay Creek

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

El Camino

10.0 out of 10, Exceptional, (33)
"Very cute cabin. We enjoyed the peace and quiet. Ver close to our destin.ation, Point lookout."
El Camino

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (57)
"My friend and I stayed for the weekend and had a lovely time. The property is quiet and secluded, and the beach area is very cute. Dog friendly is also a plus."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is €576
includes taxes & fees
20 Feb - 21 Feb
4-BR Waterfront Turret Home

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (12)
"This was a great little cottage and was perfect for our stay. We wanted to be close to Valey Lee and the location was great. We will definitely consider staying again."
2 Bedroom Cozy Beach Cottage with Beach Access

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (66)
"the Hoopers Island area is amazingly wild and beautiful. we loved the Harriet Tubman visitors center just a short trip away, and the Blackwater Refuge just incredibly beautiful. the winter birds! we learned so much about the history and culture of the lower islands.the house is more cabin style, smaller than we anticipated, but we got used to that. it was full-on winter weather and wind, so we couldn't kayak as we'd hoped, and the coast was mostly rocks so hard to walk along. it's a place for...
Waterfront Cottage in Beautiful Hoopers Island

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Hollywood you may be interested in

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 star property
7.6 out of 10, Good, (1002)
"Great place to stay"
The price is €98
includes taxes & fees
16 Mar - 17 Mar
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Springhill Suites by Marriott Prince Frederick

3.0 star property
8.6 out of 10, Excellent, (855)
"Front desk was more than helpful and provided us a late check out. Pool and hot tub were clean. Breakfast was excellent. Staff and rooms were great! bed was comfy. "
The price is €152
includes taxes & fees
16 Mar - 17 Mar
Springhill Suites by Marriott Prince Frederick
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Hollywood?

Yes, there are holiday rentals close to the most popular sights in Hollywood, or you can select a more secluded option if you're looking for a relaxing stay. Hollywood is known for its restaurants and sporting events. Make sure you have time to check out the shopping and parks during your trip.

What are some of the best holiday rentals that Hollywood has to offer?

4BDRM River front house with Private Beach in Hollywood: This highly rated holiday home rental in Hollywood is located on the beach, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Hollywood?

Choose from 3 Expedia holiday rentals in Hollywood for a memorable holiday.

What’s there to see and do in Hollywood?

Greenwell State Park and Three Notch Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Former Rowland Property and Broad Creek Community Park.

What’s a holiday rental in Hollywood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hollywood. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips.