Coastline along the Chesapeake Bay at Point Lookout State Park, Maryland

Hollywood Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

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, (51 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is HK$1,215
HK$2,510 total
includes taxes & fees
8 Jul - 9 Jul
Soul Oasis - home on the Chesapeake Bay
Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$1,682
HK$2,555 total
includes taxes & fees
2 Jul - 3 Jul
Coles Point Marina
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
9.2 out of 10, Wonderful, (9 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$1,333
HK$2,251 total
includes taxes & fees
1 Jul - 2 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Smart TV, fireplace

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"This house is great and has everything we needed. It was very clean and within walking distance of the beach and restaurants. Loved it and would book again!"
United States
Sandra S.
The price is HK$872
HK$2,846 total
includes taxes & fees
25 Jun - 26 Jun
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Interior

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (10 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is HK$1,623
HK$3,310 total
includes taxes & fees
20 Jul - 21 Jul
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"Second time here and we love the convenience to Prince Frederick and the comfort offered by the hosts. "
United States
RACHEL S.
The price is HK$2,364
HK$2,830 total
includes taxes & fees
1 Jul - 2 Jul
Cottage Located on the Patuxent River!
Property grounds

Sail Away

Sail Away
Colonial Beach
10.0 out of 10, Exceptional, (11 reviews)
"Stay was wonderful!"
United States
Karen H.
The price is HK$1,435
HK$2,895 total
includes taxes & fees
8 Jul - 9 Jul
Sail Away
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 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$1,803
HK$3,000 total
includes taxes & fees
29 Jun - 30 Jun
Bright and airy waterfront getaway
Fridge, microwave, oven, stovetop

Riverfront Home w/Dock · Fire Pit · Kids Play Area

Riverfront Home w/Dock · Fire Pit · Kids Play Area
Montross
9.6 out of 10, Exceptional, (15 reviews)
"Everything about this stay was FANTASTIC. The host was amazing, the condo was in excellent condition and the view is AMAZING! Enjoyed everything about this stay!"
United States
N C.
The price is HK$2,109
HK$4,820 total
includes taxes & fees
29 Jun - 30 Jun
Riverfront Home w/Dock · Fire Pit · Kids Play Area
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is HK$2,705
HK$3,318 total
includes taxes & fees
29 Jun - 30 Jun
2 Bedroom Cottage at 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$2,117
HK$2,568 total
includes taxes & fees
25 Jun - 26 Jun
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
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, (4 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is HK$2,689
HK$5,071 total
includes taxes & fees
25 Jun - 26 Jun
Charming Waterfront 3-bedroom house in Piney Point
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,137
HK$3,606 total
includes taxes & fees
25 Jun - 26 Jun
Plum Point Cottage #17
Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is HK$3,355
HK$7,157 total
includes taxes & fees
1 Jul - 2 Jul
'the Bayside Escape' Remote Chesapeake Bay Estate
Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$2,188
HK$4,925 total
includes taxes & fees
28 Jun - 29 Jun
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Fridge, microwave, oven, stovetop

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is HK$1,588
HK$4,152 total
includes taxes & fees
30 Jun - 1 Jul
Anne & Fred`s Leonardtown Home W/ Arcade room!
Outdoor dining

Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (36 reviews)
"Great spot"
United States
SHAWN W.
The price is HK$3,271
HK$5,819 total
includes taxes & fees
29 Jun - 30 Jun
Waterfront Reset: Views, Games, Boats & Total Calm
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$2,117
HK$2,568 total
includes taxes & fees
25 Jun - 26 Jun
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
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, (12 reviews)
"Listing was accurate; communication with host was great and helpful. We had a wonderful family time."
United States
Melissa D.
The price is HK$2,885
HK$4,854 total
includes taxes & fees
5 Jul - 6 Jul
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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

Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park

10/10 Excellent
"The property and my room were very clean. The receptionist desk staff were very friendly and helpful. I would highly recommend and will stay there again if I’m in the area."
Dean 2-night trip
Posted 2 hours ago
Spark by Hilton California Lexington Park

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?

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay: This holiday home rental outside of Hollywood is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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 Barrett Island.

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.