Hollywood Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Hollywood holiday rentals

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is HK$1,058
HK$2,301 total
includes taxes & fees
4 May - 5 May
Soul Oasis - home on the Chesapeake Bay
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is HK$1,199
HK$2,069 total
includes taxes & fees
30 Apr - 1 May
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Smart TV

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Colonial Beach
9.4 out of 10, Exceptional, (12 reviews)
"We stayed for 2 nights in the fall for a family event at Stratford Harbor. The house was pristine and cozy. Loved the fenced backyard for the pets and the walk ability of the town. The host and back up host were VERY responsive."
United States
Saundra B.
The price is HK$692
HK$2,619 total
includes taxes & fees
4 May - 5 May
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,332
HK$3,436 total
includes taxes & fees
28 Apr - 29 Apr
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Outdoor dining

Waterfront Reset—Kayaks, Games, Views & Total Calm

Waterfront Reset—Kayaks, Games, Views & Total Calm
Montross
10.0 out of 10, Exceptional, (31 reviews)
"Great spot"
United States
SHAWN W.
The price is HK$1,608
HK$3,763 total
includes taxes & fees
28 Apr - 29 Apr
Waterfront Reset—Kayaks, Games, Views & Total Calm
Beach

Sail Away To

Sail Away To
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"Perfect location and perfect property! The condo was great for our anniversary! The furnishings and amenities were top notch! We would go back again 100%. Recommend renting a golf cart. All of the places to eat are locally owned supporting small business in this community is a great feeling! The owner was so great to communicate with, so very helpful! "
United States
Katherine C.
The price is HK$1,097
HK$2,460 total
includes taxes & fees
13 May - 14 May
Sail Away To
Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$1,868
HK$3,423 total
includes taxes & fees
28 Apr - 29 Apr
Coles Point Marina
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is HK$2,116
HK$2,566 total
includes taxes & fees
28 Apr - 29 Apr
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is HK$2,292
HK$2,720 total
includes taxes & fees
28 Apr - 29 Apr
Cottage Located on the Patuxent River!
Smart TV, books

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is HK$1,677
HK$3,414 total
includes taxes & fees
28 Apr - 29 Apr
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Fridge, microwave, oven, stovetop

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is HK$1,763
HK$4,243 total
includes taxes & fees
28 Apr - 29 Apr
Anne & Fred`s Leonardtown Home W/ Arcade room!
Fridge, microwave, oven, stovetop

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (15 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is HK$846
HK$3,206 total
includes taxes & fees
28 Apr - 29 Apr
Luxury Modern Waterfront Retreat
Interior

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (8 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is HK$1,450
HK$3,069 total
includes taxes & fees
28 Apr - 29 Apr
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Sun-loungers, beach towels

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is HK$1,345
HK$3,722 total
includes taxes & fees
4 May - 5 May
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Smart TV, books

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is HK$1,489
HK$3,418 total
includes taxes & fees
28 Apr - 29 Apr
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is HK$2,186
HK$4,020 total
includes taxes & fees
28 Apr - 29 Apr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Interior

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (19 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is HK$1,622
HK$2,782 total
includes taxes & fees
30 Apr - 1 May
Bright and airy waterfront getaway
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is HK$2,703
HK$3,316 total
includes taxes & fees
28 Apr - 29 Apr
2 Bedroom Cottage at Coles Point Marina
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is HK$2,116
HK$2,566 total
includes taxes & fees
28 Apr - 29 Apr
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is HK$2,413
HK$4,612 total
includes taxes & fees
29 Apr - 30 Apr
Charming Waterfront 3-bedroom house in Piney Point
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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Top Hollywood Hotel Reviews

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

8/10 Good
"Breakfast was great, room was clean. The only issue I had was hearing the guests above Or below my me running around in the room 7am in the morning . "
Valarie 1-night trip
Posted 1 hour ago
Springhill Suites by Marriott Prince Frederick

Find out more about Hollywood

Search for holiday rentals in Hollywood on Expedia! You can easily find your home rentals, villas, holiday apartments in Hollywood using one of the methods below:

  • View our selection of featured holiday rentals in Hollywood
  • Use the map to find apartments and other holiday homes in the Hollywood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hollywood while they last

Look no further and take a look at our great range of rental properties in Hollywood!

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?

Quaint waterfront home with private beach: This holiday home rental outside of Hollywood is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease 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. You can relax into your holiday with a patio and a selection of games.

How many holiday rentals will I find in Hollywood?

Choose from 4 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 Michael P. O'Brien Athletics and Recreation Center, or get out into nature at a spot like Three Notch Park. In the wider area, you’ll find Greenwell State Park and Jefferson Patterson Park and Museum.

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.