Holiday houses in Upper Falls

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Top-rated holiday rentals in Upper Falls

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

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Guest favourite

Home in Middle River

4.95 out of 5 average rating, 37 reviews

Waterfront Home with Private Beach, Stunning Views

GraceRating, 5 stars1 month ago

We stayed in George’s home to celebrate our father’s 90th birthday and had a lovely time. All rooms were very clean, the beds were comfortable, and the kitchen was fully stocked. The view out back over the water, especially at sunrise, was beautiful. The neighborhood was quiet and safe. Excellent communication and support! Thank you, George!

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 149 reviews

Waterfront Chesapeake Bay Sunrises w/Private Pier!

EricRating, 5 stars1 month ago

Comfortable and cozy cottage on the water. The back deck and enclosed porch was super nice and the view was amazing. Had it not been so cold during our stay we would have been outside more. Everything was as described and perfect for the two of us and my mom. The dock was easily accessible which was nice. Great stay and close to our Son we were there to visit.

Guest favourite

Home in Stevensville

4.9 out of 5 average rating, 42 reviews

Beachside Dream

MelanieRating, 5 stars1 month ago

BK's home is a gorgeous winter getaway. The architecture is striking, and the wall of windows facing the water made us feel as if we were outdoors, even though we were cozied up on the couch. The area trails are pretty and dog friendly. We enjoyed a gorgeous waterfront sunset while sitting around the backyard fire pit. The house is clean and spacious, and the kitchen was well stocked with pots, pans, and other equipment. The wifi was strong and reliable, too. The beds are comfy and the showers work well. We would definitely return.

Guest favourite

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars2 months ago

The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !

Guest favourite

Home in Centreville

5 out of 5 average rating, 22 reviews

Water Oasis on the Eastern Shore

KatjaRating, 5 stars4 months ago

This is a beautiful property with all the amenities our group of 11 college friends needed to catch up and relax together. We loved morning coffee on the screened in porch and lounging around the pool. New hot tub was also a big bonus. Plenty of room for everyone to sleep and lounge comfortably. Thank you so much!

Superhost

Cottage in Pasadena

4.88 out of 5 average rating, 121 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

AlexaRating, 5 stars3 months ago

A nice stay with family. If you know what to expect it’s a lovely stay. The cottages are small but the scenery is beautiful. A little run down but perfectly fine just for sleeping for a weekend. We did encounter a lot of flies but we were right on the water. Overall a good stay. Definitely visit Tuggies if you love a good dive bar!

Guest favourite

Home in Annapolis

4.93 out of 5 average rating, 108 reviews

Historic Downtown House with Off Street Parking

LisaRating, 5 stars2 months ago

Christopher’s place in downtown Annapolis is perfectly located! There are so many great shops and restaurants in walking distance. The off street parking was so convenient. The house itself is so cozy with very comfortable beds and nice towels and linens. The decor is tastefully done and the kitchen was well equipped with everything we needed to cook Thanksgiving dinner. Our family, including our beloved Golden Retriever, had a great time! For others traveling with a dog, just know that the yard is not fully fenced… the walkway by the house is open to the street and the rear yard is connected to a shared parking area…so you will need to keep a close eye on your dog. Overall we were so happy with our stay and would love to stay again. Thanks, Christopher, for sharing your home in one of our favorite places to visit. We will be back!

Guest favourite

Home in North East

5 out of 5 average rating, 16 reviews

Heron Creek- Historic home on Main Street

PaulRating, 5 stars2 months ago

This house exceeded our expectations. This is one of the rare times when the rental looks even better in person than in the pictures. The house was extremely clean, well maintained, and the beds were very comfortable. It was cozy for hanging out and the kitchen well appointed. The location is great too. It was easy to find and park there. There are lots of businesses within walking distance and a water-side park nearby (~ 3/4 mile) for morning walks. It wasn't too far to Elk Neck State Park for a beautiful hike. We were in the area for Thanksgiving, but are already discussing the possibility of coming back in spring or summer to explore more of the area. Last, the hosts were quickly responsive when we communicated a need.

Holiday rentals for every style

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Popular amenities for Upper Falls holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Upper Falls

Guest favourite

Home in Edgewater

4.91 out of 5 average rating, 139 reviews

House in Edgewater Maryland

StephanieRating, 5 stars3 months ago

The place was exactly what we needed. Location was perfect to get to everything we needed and wanted to do. We were able to check in a little bit early, which was amazing and helpful. Would definitely stay again!

Guest favourite

Home in Gettysburg

4.95 out of 5 average rating, 110 reviews

East Cavalry Red House

SagarRating, 5 stars2 months ago

Jeff and Patty’s home is absolutely amazing! From the moment we arrived, we felt welcomed and at ease. The house is beautifully maintained with so much character, filled with fascinating historical books and charming frames that added to the unique experience. The fireplace was a highlight—it kept us warm and cozy throughout our stay. Jeff and Patty were wonderful hosts, always available and attentive, ensuring we had everything we needed. Their care and attention to detail made our stay truly special. We had such a great time and are already looking forward to returning in the spring. Thank you, Jeff and Patty, for sharing your incredible home with us!

Superhost

Home in Wye Mills

4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

LisaRating, 5 stars8 months ago

Kevin is a great host to us year after year! we love staying at his place!

Guest favourite

Home in Fairfield

4.98 out of 5 average rating, 63 reviews

Lake Front 5 Bedrm Home, by Liberty Mt Ski Resort

ChristineRating, 5 stars3 weeks ago

Beautiful, spacious home with plenty of room for the entire family. Close to many different attractions from Gettysburg to Liberty Mountain.

Superhost

Home in Pasadena

4.85 out of 5 average rating, 54 reviews

Beautiful New Home Near Beach and Patapsco River

VeronaRating, 5 stars2 months ago

House looks even better than the pictures. Very nice, very modern and all amenities were wonderful. I am looking to come back in the summer and enjoy the lovely pool area.

Guest favourite

Apartment in Canton

5 out of 5 average rating, 27 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

KimberlyRating, 5 stars4 weeks ago

Very responsive host. Apartment in fabulous location. In wonderful historic Baltimore house and neighborhood. Minor glitches addressed immediately and easily by host. If you’re looking for something fun and interesting this is it.

Guest favourite

Home in Strasburg

4.95 out of 5 average rating, 403 reviews

Pine wood retreat

JeffRating, 5 stars1 month ago

Pinewood Retreat was the perfect place for our family to spend Christmas. We felt right at home. The common areas are great for entertaining and the kitchen was well stocked so we were able to cook Christmas dinner. Our parents came for Christmas Eve and Christmas dinner so we had 10 people total and there weren’t quite enough forks and knives but that’s a tiny complaint considering what a nice house and beautiful location this is. The teenagers really enjoyed the hot tub. The beds were comfortable. All around a great place to stay when visiting Lancaster County!

Superhost