House holiday rentals in Hollywood, St. Mary's County

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Popular amenities for house rentals in Hollywood, St. Mary's County

House rentals with a pool

Guest favourite
Home in Montross
4.97 out of 5 average rating, 89 reviews

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks

CourtneyRating, 5 stars3 weeks ago
Andrea was so responsive from day 1 when I had questions about the house! We had 10 people in town for a wedding and her house was only 3 miles from the venue which was ideal! The house was clean and had nice little extra touches; the bottom floor was surprisingly spacious and perfect for hanging out! And the hot tub was a nice add also! Overall, it was a great experience!
Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 116 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars3 weeks ago
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.
Guest favourite
Home in Lusby
4.91 out of 5 average rating, 81 reviews

Spacious and private waterfront, sleeps 10

MichaelRating, 5 stars2 months ago
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.
Top guest favourite
Home in Lusby
5 out of 5 average rating, 19 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

AlanRating, 5 stars5 days ago
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!
Guest favourite
Home in Montross
4.99 out of 5 average rating, 156 reviews

Beach Please! River cottage w/private beach & dock

LisaRating, 5 stars2 weeks ago
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.
Superhost
Home in Port Republic
4.78 out of 5 average rating, 23 reviews

Family Friendly: Hot Tub, Grill, Pool & More!

TakishaRating, 5 stars3 weeks ago
This was one of the most well equipped houses I have ever stayed in. The hosts were very easy to communicate with and responded quickly to each contact. I highly recommend this place!!
Guest favourite
Home in Fort Washington
4.92 out of 5 average rating, 156 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

TheresaRating, 5 stars1 week ago
Daniel’s Home was beautiful and he made this special event for me and my family able to celebrate my sons 26th Heavenly Birthday a success We were very comfortable and it really felt like home the pool was very clean and the Home was very spacious and squeaky clean I would love to Book Daniel again He was a very nice and friendly Host that responded to any questions we had he made communication easy me and my family really enjoyed our self and yes he’s reasonable and you definitely get what you paid for and more Thank you again Daniel
Guest favourite
Home in Montross
4.94 out of 5 average rating, 53 reviews

Brigadoon, the BRAND NEW Waterfront Haven

LiviaRating, 5 stars4 days ago
This house was perfect for our family mini vacation. The view was incredible, the house was stocked with all sorts of thoughtful extra touches. We loved the kayaks, paddle boards, tubes and beach area. Pam was so helpful and responsive. Everyone had a great time!

Weekly house rentals

Guest favourite
Home in Saint Leonard
4.96 out of 5 average rating, 95 reviews

Large home w/ 6 bedrooms, 2 kitchens, and hot tub!

MeredithRating, 5 stars1 month ago
It was a great place to stay for a mini-family gathering! Shelly even provided a booklet with local restaurants and activities in the area.
Guest favourite
Home in Newburg
4.96 out of 5 average rating, 70 reviews

Beautiful, serene waterfront property

JonathanRating, 5 stars1 month ago
An incredible peace of property! This house has been beautifully renovated and exceeded every expectation. Unbelievable waterfront views from nearly every room in the house, back porch and fire pit. Also a very nice surprise of having a little play area stocked with toys for the little ones! This is a must stay if we’re ever back in the area!
Guest favourite
Home in Prince Frederick
4.9 out of 5 average rating, 10 reviews

Chesapeake Escape

LuzRating, 5 stars3 days ago
We had a great stay! The place was really clean and had great views of the beach.
Guest favourite
Home in Montross
4.91 out of 5 average rating, 22 reviews

Potomac River Getaway

SkyRating, 5 stars2 weeks ago
Had a great weekend in the Northern Neck here! We watched a pod of dolphins and stingrays from the backyard, enjoyed easy access to nearby parks, and had a great time cooking in the kitchen. This is seemingly a very recently renovated house, and all the towels, sheets, beds, etc. seemed brand new as well. It was super clean, super comfy, and the hosts were very responsive! I liked that the property was surrounded on one side by forest as well—it was nice and quiet and secluded. Finally, they have a super cute collection of board games disguised as old timey books. I'd definitely stay here again!
Superhost
Home in Saint Leonard
4.75 out of 5 average rating, 12 reviews

Waterfront! The River's Roost on the Patuxent!

AlexandrosRating, 5 stars4 months ago
My wife, 4 year old son and I enjoyed a week at John’s beautiful home on the Patuxent River. The house and property were perfect and the views were amazing every day. The house had everything we needed and we felt right at home. He was very responsive and helpful when we had questions. We look forward to staying here again in the summer!
Top guest favourite
Home in Solomons
4.99 out of 5 average rating, 78 reviews

Solomons home with harbor view!

GingerRating, 5 stars2 weeks ago
This was our first visit to Solomon’s Island and the location of this home was perfect. Mother uses a rollator for walking and could easily walk from the house to the boardwalk daily. We spent many hours on the second floor covered deck enjoying the activity at the harbor. Terri gave us good upfront information to help us prepare for our stay. The home was clean, quiet, and comfortable.
Superhost
Home in Piney Point
4.81 out of 5 average rating, 52 reviews

2 Bedroom Cozy Beach Cottage

WillieRating, 5 stars1 month ago
Michelle is a great host. The place is clean and has many conveniences. I highly recommend!
Top guest favourite
Home in Lusby
4.93 out of 5 average rating, 15 reviews

Riverview Retreat

Helena LightRating, 5 stars4 weeks ago
This served as a low key weekend retreat for us. We unplugged and enjoyed being in each other’s company. Being on the river, surrounded by trees and birdwatching was exactly what we needed. The kitchen was well appointed so we were able to enjoy family favorite activities (cooking together and playing board games).

Private house rentals

Guest favourite
Home in Solomons
4.96 out of 5 average rating, 28 reviews

Solomons Yellow House - Waterfront

BeckyRating, 5 stars2 weeks ago
Came to Solomon’s for a wedding . Had a wonderful stay at John’s Place. All the comforts of home. Very clean, Fantastic location- easy walk to restaurant’s, shops, And Mass on Sunday ! Beautful water front property. Lovely decor- excellent kitchen space. Lovely the unique lighting, screened -in porch, and front porch! Very Comfy beds. Would def stay here again!!
Top guest favourite
Home in Lexington Park
5 out of 5 average rating, 10 reviews

Stunning Views, Remodeled Family-Friendly Home

TammiRating, 5 stars4 days ago
This was a truly lovely and clean home. Staying there was so wonderful - sitting on the screened porch listening to the water, walking the waterfront, lovely. It was so peaceful and calming of a location. Also, walking or biking distance to the St. Marys college and historical park. I recommend anyone stay there - I would again. We felt so comfortable and welcomed into this gorgeous waterfront property. You cannot beat the views and location. Communicative hosts. Thanks for a great stay!
Top guest favourite
Home in Port Republic
5 out of 5 average rating, 38 reviews

Coastal Haven- Beach w/ BBQ

KarenRating, 5 stars1 month ago
My family had a wonderful stay at this BNB. Lots of space for everyone. Big rooms, really nice kitchen. It was very neat and clean. The neighborhood access to the beach was a plus. The neighborhood is very nice and convenient to the highway.
Superhost
Home in Lusby
4.88 out of 5 average rating, 43 reviews

Waterfront home with three bedrooms,3 full baths

AlyssaRating, 5 stars1 week ago
Really great place with all the amenities of home!
Guest favourite
Home in Montross
4.96 out of 5 average rating, 76 reviews

Waterfront home, private dock

ShufanRating, 5 stars3 weeks ago
We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.
Guest favourite
Home in Montross
4.95 out of 5 average rating, 66 reviews

Luxury Modern Waterfront Retreat

MalikRating, 5 stars3 weeks ago
Kelly and Thomas were amazing host. Very responsive and accommodating The home was very clean and the location was great.. 10/10. Definitely would book again!
Top guest favourite
Home in Hague
5 out of 5 average rating, 22 reviews

Rivah view get away

HollyRating, 5 stars3 weeks ago
We were in the area to explore George Washington’s Birthplace and Stratford hall and had a lovely stay at Susan’s place. The beds were comfortable, we cooked and sat on the front porch listening to the rain. The tavern is within walking distance but we didn’t get a chance to go. Hoping to come back again because the area is fabulous!
Guest favourite
Home in Lusby
4.89 out of 5 average rating, 97 reviews

SoMD Waffle House 1.5 acres of cozy coastal living

MarkRating, 5 stars1 week ago
We really enjoyed our stay here. It was relaxing and super chill.

Quick stats about house rentals in Hollywood, St. Mary's County

  • Total rentals

    30 properties

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore

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