A coastal landscape with a rocky shoreline, a sandy beach, and a clear blue sky.

Holiday Homes in Hollywood

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Our top choices for Hollywood holiday homes

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is NZ$457
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,256
includes taxes & fees
28 Sept - 29 Sept
4-BR Waterfront Turret Home

3. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is NZ$616
includes taxes & fees
28 Sept - 29 Sept
Bright and airy waterfront getaway

4. 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, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is NZ$674
includes taxes & fees
1 Oct - 2 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

5. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is NZ$832
includes taxes & fees
29 Sept - 30 Sept
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

6. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is NZ$1,482
includes taxes & fees
28 Sept - 29 Sept
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

7. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is NZ$2,057
includes taxes & fees
28 Sept - 29 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub

8. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is NZ$1,739
includes taxes & fees
29 Sept - 30 Sept
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

9. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful location "
United States
Jonathan M.
The price is NZ$1,457
includes taxes & fees
26 Oct - 27 Oct
2 Acre Oasis with Private Beach! Family and dog friendly!

10. Waterfront Game-Themed Getaway · Dock & Kayaks

Waterfront Game-Themed Getaway · Dock & Kayaks
Montross
10.0 out of 10, Exceptional, (40 reviews)
"Very comfortable beds and living spaces, and can accommodate large groups and handicapped!"
United States
Amanda B.
The price is NZ$855
includes taxes & fees
28 Oct - 29 Oct
Waterfront Game-Themed Getaway · Dock & Kayaks

11. 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 NZ$803
includes taxes & fees
27 Oct - 28 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

12. 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
9.6 out of 10, Exceptional, (14 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is NZ$565
includes taxes & fees
13 Oct - 14 Oct
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

13. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is NZ$810
includes taxes & fees
1 Oct - 2 Oct
Plum Point Cottage #17

14. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 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 NZ$1,281
includes taxes & fees
19 Oct - 20 Oct
Charming Waterfront 3-bedroom house in Piney Point

15. 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 NZ$571
includes taxes & fees
28 Sept - 29 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

16. 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 NZ$525
includes taxes & fees
28 Sept - 29 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

17. 'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay. They house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
United States
Bridget C.
'The Bayside Escape' Remote Chesapeake Bay Estate
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

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Hollywood Holiday Homes information

Number of reviews
220
Accommodation
264 Holiday Homes
Lowest Price
NZ$457
Highest Price
NZ$2,057