Vacation rentals in Hollywood

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Top-rated vacation rentals in Hollywood

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!

Mar 19 – 26

G$26,857 GYD per night
Guest favorite

Apartment in California

4.91 out of 5 average rating, 182 reviews

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

May 26 – Jun 2

G$32,941 GYD per night
Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

This beach cottage sits just across the street from the Chesapeake Bay on the Western Shore. You'll have access to two private community beaches where you can sit, relax, and just enjoy the scenery. If you are an early riser, you can enjoy beautiful sun rises over the bay. If you search the sand, you might even find fossils, including shark teeth! Close proximity to Washington DC, Annapolis, and Baltimore. There are a lot of local restaurants and shopping. You will not be disappointed.

Oct 25 – Nov 1

G$32,262 GYD per night

Popular amenities for Hollywood vacation rentals

Stay near Hollywood's top sights

Harris Teeter18 locals recommend
Cracker Barrel Old Country Store4 locals recommend
R/C Lexington Exchange Movies 128 locals recommend
Texas Roadhouse7 locals recommend
Red Robin Gourmet Burgers and Brews4 locals recommend
Myrtle Point Park14 locals recommend

Other great vacation rentals in Hollywood

Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 292 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Oct 5 – 12

G$17,268 GYD per night
Guest favorite

Apartment in Lexington Park

4.93 out of 5 average rating, 187 reviews

Private apartment with kitchenette

Jan 18 – 25

G$13,220 GYD per night
Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 159 reviews

Madison Nature Getaway

Oct 22 – 29

G$25,878 GYD per night
Guest favorite

Cottage in Leonardtown

4.93 out of 5 average rating, 125 reviews

Breton Breeze

Jan 17 – 24

G$32,584 GYD per night
Guest favorite

Cabin in Lusby

4.94 out of 5 average rating, 139 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

Jul 14 – 21

G$68,179 GYD per night
Guest favorite

Guest suite in Colonial Beach

4.97 out of 5 average rating, 257 reviews

Bayview Bungalow

Jan 8 – 15

G$24,032 GYD per night
Guest favorite

Cottage in Colonial Beach

4.93 out of 5 average rating, 177 reviews

Cozy cottage 3 blocks from beach

Jan 13 – 20

G$25,697 GYD per night
Guest favorite

Home in Hollywood

4.83 out of 5 average rating, 24 reviews

Riverhouse

Dec 9 – 16

G$24,275 GYD per night
Guest favorite

Cottage in Hollywood

5.0 out of 5 average rating, 31 reviews

Cottage on the Creek

Feb 3 – 10

G$54,238 GYD per night
Guest favorite

Home in Leonardtown

4.95 out of 5 average rating, 39 reviews

Old Bay Inn

Aug 31 – Sep 7

G$27,795 GYD per night
Guest favorite

Apartment in Leonardtown

4.94 out of 5 average rating, 33 reviews

Retreat at Fenwick

Sep 29 – Oct 6

G$25,556 GYD per night
Guest favorite

Place to stay in California

4.88 out of 5 average rating, 8 reviews

Modern | Bright | Cozy Private Room | Free Parking

Dec 6 – 13

G$10,356 GYD per night

Quick stats about vacation rentals in Hollywood

Total rentals

60 properties

Wifi availability

50 properties include access to wifi

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.9K reviews

Frequently Asked Questions

  • What are the most popular amenities for House Rentals in Hollywood?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with air conditioning, over 20 homes with free parking, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Hollywood have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Hollywood. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Hollywood?

    Yes! Work meets play with ease at over 30 vacation rentals in Hollywood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do bed and breakfast rentals in Hollywood have air conditioning?

    Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Hollywood. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in bed and breakfast rentals in Hollywood?

    Experience the best of Hollywood with our bed and breakfast rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Hollywood?

    Four-legged friends are welcome in Hollywood. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do bed and breakfast rentals in Hollywood have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Hollywood. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Hollywood?

    Hollywood has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. St. Mary's County
  5. Hollywood