Holiday Rentals in Hollywood

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Holiday Rentals in Hollywood

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

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

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

10.0 out of 10, Exceptional, (38)
"Heather and Ed are superb hosts. The home was very clean, well stocked and in the perfect location! "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is €305
includes taxes & fees
2 Dec - 3 Dec
Soul Oasis - home on the Chesapeake Bay

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (63)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island

The Schultz Estate

8.8 out of 10, Excellent, (14)
"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

Chic Cottage w/ Private Yard: Steps to Beach!

10.0 out of 10, Exceptional, (16)
"Amazing use of square footage to provide everything a couple could use for a getaway. Owners have great taste and decorations give it a beach vibe. Conveniently located at the Point and walking distance to bars and restaurants. Would stay here again."
Chic Cottage w/ Private Yard: Steps to Beach!

Cozy Virginia Potomac Riverfront Cottage

9.8 out of 10, Exceptional, (34)
"This is a nice little cottage, tucked away from everything right on the river. I was looking for some peace and quiet, and that’s exactly what I got. Even though the weather wasn’t great, the sunroom still let me enjoy the views. "
Cozy Virginia Potomac Riverfront Cottage

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

Belle of the Chesapeake Bay

9.6 out of 10, Exceptional, (9)
"We initially booked due to location (we have family in the neighborhood). We are so glad we did! The property had plenty of space for 6 and offered rest and relaxation after a busy wedding weekend. The only con I can think of with the property is that all bathrooms are on the smaller side. The comfort, convenience, and amenities offered far outweighs this. This property is sure to become our go to when visiting the area. "
Belle of the Chesapeake Bay

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!

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

El Camino

10.0 out of 10, Exceptional, (31)
"The place was phenomenal. Very clean. Very awesome to stay there. If you ever want to see the most beautiful sunset you have to go there. Plus the fishing was a lot of fun. Me and my husband really enjoyed the few days that we were there. Communication very good people. Very nice! That stayed next to us. I would definitely go back"
El Camino

Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

10.0 out of 10, Exceptional, (43)
"Great time! First time in Colonial Beach. Low key family time. House was perfect location for us. Very enjoyable!"
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (39)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Mid-Century Modern and Marvelous on the Bay

10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay

Private Retreat Bungalow-One Level, 2 blocks from Beach w/Porch & Deck

10.0 out of 10, Exceptional, (28)
"The house is just as the pictures show. Very clean, comfortable and a short drive to the beach. Quiet neighborhood and very nice neighbors."
Private Retreat Bungalow-One Level, 2 blocks from Beach w/Porch & Deck

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (182)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is €476
includes taxes & fees
1 Dec - 2 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (10)
"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...
Historic Hoopersville Getaway on Chesapeake Bay!
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

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 star property
7.6 out of 10, Good, (1058)
"Very nice rooms but the breakfast is average. "
The price is €94
includes taxes & fees
30 Nov - 1 Dec
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, (834)
"The staff are lovely, and the rooms are spacious, clean, and modern. The hotel is very nice. "
The price is €108
includes taxes & fees
23 Dec - 24 Dec
Springhill Suites by Marriott Prince Frederick

River Edge Inn

2.5 star property
8.2 out of 10, Very good, (249)
"The Inn is right in front of the water. There are a few spots that you can have a drink and enjoy the scenery."
The price is €79
includes taxes & fees
10 Dec - 11 Dec
River Edge Inn
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?

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**: This holiday home rental outside of Hollywood is located on the waterfront, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and an arcade/games room.

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?

Explore the area and family-friendly sights such as R&J's PlayPark, or get out into nature at a spot like Greenwell State Park. In the wider area, you’ll find Calvert Cliffs State Park and Patuxent River Naval Air Station.

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.