Vacation rentals in Hollywood

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Top-rated vacation rentals in Hollywood

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Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 301 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!

Aug 25 – Sep 1

€ 145 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 21 – 28

€ 164 per night

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

Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Jul 14 – 21

€ 88 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 22 – 29

€ 167 per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 192 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Mar 3 – 10

€ 108 per night

Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 208 reviews

Peaceful Waterfront Retreat on The Bay

This is a serene, waterside cabin with a private dock, nestled on quiet St. Leonard Creek about one hour outside of Washington, DC. You will enjoy a close quarters stay in this rustic studio cabin, and it is the perfect getaway for anyone looking for some peace and quiet. Come on your own to finally get some work done, or bring your family to enjoy the outdoors! We have two kayaks and two canoes. The house is great for up to two couples looking to catch up and explore the surrounding area.

Oct 20 – 27

€ 174 per night

Guest favorite

Apartment in Lexington Park

4.98 out of 5 average rating, 102 reviews

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Sep 19 – 26

€ 78 per night

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 310 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Aug 27 – Sep 3

€ 139 per night

Guest favorite

Apartment in Leonardtown

4.98 out of 5 average rating, 119 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

Sep 26 – Oct 3

€ 159 per night

Guest favorite

Guesthouse in Bushwood

4.92 out of 5 average rating, 143 reviews

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Feb 24 – Mar 3

€ 100 per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 313 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Feb 9 – 16

€ 96 per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 536 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Kayaks and bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

Mar 7 – 14

€ 154 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Hollywood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Cottage in Leonardtown

4.93 out of 5 average rating, 127 reviews

Breton Breeze

Sep 29 – Oct 6

€ 181 per night

Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 123 reviews

Beach Front and 'Perfectly Placed'

Oct 18 – 25

€ 208 per night

Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 161 reviews

Madison Nature Getaway

Aug 5 – 12

€ 127 per night

Guest favorite

Guest suite in Colonial Beach

4.97 out of 5 average rating, 261 reviews

Bayview Bungalow

Dec 16 – 23

€ 141 per night

Guest favorite

Place to stay in California

4.89 out of 5 average rating, 9 reviews

Modern | Bright | Cozy Private Room | Free Parking

Mar 4 – 11

€ 64 per night

Guest favorite

Home in Hollywood

4.84 out of 5 average rating, 25 reviews

Riverhouse

Jun 11 – 18

€ 134 per night

Guest favorite

Cottage in Hollywood

5.0 out of 5 average rating, 31 reviews

Cottage on the Creek

Jan 15 – 22

€ 291 per night

Guest favorite

Apartment in Leonardtown

4.94 out of 5 average rating, 34 reviews

Retreat at Fenwick

Aug 19 – 26

€ 139 per night

Show all

Quick stats about vacation rentals in Hollywood

Total rentals
60 properties
Wifi availability
60 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
30 properties are a good fit for families
Total number of reviews
2K 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 wifi, over 30 homes with free parking, over 30 homes with air conditioning, 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 house rentals in Hollywood have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Hollywood. Enjoy a tailored experience with all the comforts you desire.
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 house rentals in Hollywood have wifi?
Absolutely! We offer over 30 house 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 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Hollywood have free parking?
Absolutely! We offer over 30 house rentals with free parking in Hollywood. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Hollywood

Top-rated vacation rentals in Hollywood

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Hollywood vacation rentals

Stay near Hollywood's top sights

Other great vacation rentals in Hollywood

Cottage in Leonardtown

Cottage in Leonardtown

Farm stay in Madison

Guest suite in Colonial Beach

Place to stay in California

Home in Hollywood

Cottage in Hollywood

Apartment in Leonardtown

Quick stats about vacation rentals in Hollywood

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

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

Do house rentals in Hollywood have a kitchen?

Are there vacation rentals with a dedicated workspace in Hollywood?

Do house rentals in Hollywood have air conditioning?

Are there pet-friendly vacation rentals in Hollywood?

Do house rentals in Hollywood have wifi?

Are there family-friendly vacation rentals in Hollywood?

Do house rentals in Hollywood have free parking?

Destinations to explore