
Apartment holiday rentals in Oakland
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Top-rated apartment rentals in Oakland
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Apartment in Davis
4.81 out of 5 average rating, 124 reviewsThe Drifter, A Sustainable Cozy One Bedroom
JessRating, 5 stars7 months ago
enjoyed our stay - great location, unique and comfortable apartment, responsive host; thanks!
Superhost

Apartment in Addison
5 out of 5 average rating, 3 reviewsLake Happiness - No Wake Zone Unit 1 of 3
AlyssaRating, 5 stars11 months ago
We had another great stay at the No Wake Zone! The two bedroom offers some additional space and a beautiful view. Such a convenient, well kept spot for a weekend on the Yough!
Superhost

Apartment in Davis
4.8 out of 5 average rating, 56 reviewsBlackwater Bed & Bikes 4
AmandaRating, 5 stars3 weeks ago
Perfect location- comfortable vibe. Lovely decor. Alison was superb. The bed was comfortable. We loved walking to all the things. Our car didn’t move! However, with the convenience of being in town and able to walk anywhere comes noise. Typically I wouldn’t turn a TV on, so not having one wouldn’t be an issue, however I would have loved to have one to drown out the neighbors conversations. Literally, someone sneezed in another unit (or upstairs) and I said, bless you. They responded saying, “thanks.” 2 things would have made our stay perfect, a white noise machine, tv or Bluetooth speaker to drown out the noise and provide some semblance of privacy and a full-length mirror in the bedroom. Overall, I would recommend this place and will likely stay again. The convenience of being right in town coupled with the river and fire pits right outside was awesome. Next time, I will pack earplugs and a speaker!
Guest favourite

Apartment in Davis
4.93 out of 5 average rating, 68 reviewsUptown Heart of Davis
BarbaraRating, 5 stars1 month ago
Great stay in Davis. Unit was exactly as pictured. Very clean and had everything we needed. Allison was quick to respond when we reached out to her with questions. Davis is a great jumping off point for many outdoor recreation activities in the area. Will stay here again if we come back for more fun and have already recommended this apartment to family and friends when they come out this way.

Apartment in Frostburg
4.8 out of 5 average rating, 85 reviewsNamaStay Studio
SamRating, 5 stars2 months ago
I appreciated how helpful Patrick was. I need some clarification on the instructions and he responded much quicker than I expected. The bed was honestly more comfortable than mine at home. Great value for the price!
Superhost

Apartment in Frostburg
4.33 out of 5 average rating, 6 reviewsThe Suite on Main Street
JohnathonRating, 5 stars7 months ago
Beautiful spot right on Main Street. Very clean and tidy. Has a wonderful pizza place downstairs. Very good location!
Superhost

Apartment in Addison
5 out of 5 average rating, 3 reviewsLovin' Lake Life - No Wake Zone Unit 3 of 3
AmandaRating, 5 stars9 months ago
Carol was very accommodating. Upon arrival a storm had just went through and the facility lost power. Carol apologized and communicated well. She even offered a full refund. Set a bucket water outside of the door in case we needed it for the bathroom. Power was restored quickly. Room was small, but accurately described. Cute and clean. Even came with towels and wash cloths and bed sheets. Ample pillows. Shampoo etc. provided. Bed was comfortable. 10/10 recommend and would stay here again!
Guest favourite

Apartment in Davis
4.88 out of 5 average rating, 78 reviewsBlackwater Bed & Bikes 5
LindsayRating, 5 stars3 weeks ago
Blackwater Bed & Bikes was a great home base for exploring Davis! The apartment was clean and cozy. The host was super responsive and was on-site within 5 minutes when we had an issue, which she resolved quickly and cheerfully. She also proactively provided drinking water for us during a boil water advisory. The location is even better than the pictures and description. Great fire pits, a big grassy area for pups, and a gravel walking path right along the river. The town is super close and we took advantage of the restaurants and shops every day. They just opened a brand new dog-friendly outpost of Big Timber Brewing right next door, with great beers and good hours. You can also hike right into Blackwater Falls State Park - one of the viewing points for the waterfall was only an easy 2.5 mile walk from the property. Would stay again in a heartbeat.
Private apartment rentals
Superhost

Apartment in Midlothian
4.85 out of 5 average rating, 13 reviewsStudio Apartment near FSU
AmelieRating, 5 stars2 days ago
Absolutely amazing place to stay right off of the highway! Felt right at home and was amazed at how comfy the bed was.
Superhost

Apartment in Davis
4.77 out of 5 average rating, 43 reviewsBase Camp
CarolineRating, 5 stars4 months ago
This was a great place to stay, especially if you are exploring the Blackwater State Park area. Couldn’t be more convenient! We were so pleasantly surprised by the shops and restaurants in the area. The food and the service from the locals cultivated a super friendly environment. The owner was very responsive over messaging the few times we reached out. Couple cons: I will say the listing was a little overpriced for what you get, though the inflated price could have been because of the holiday weekend. The upstairs bedroom would get pretty warm and there were instructions that you could not adjust the thermostat. I can understand the owner not wanting us to mess with the room temperature, the weather dropped from 51 to 11 degrees in a matter of 24 hours while we were there! But if you are a hot sleeper and being able to adjust the thermostat is important to you, it may be something worth considering! Overall I would recommend this listing!
Top Guest favourite

Apartment in Aurora
5 out of 5 average rating, 7 reviewsAlice’s Place
DerekRating, 5 stars3 weeks ago
Staying here was an absolutely peaceful and relaxing experience. From the minute we arrived we felt more than at home, it was perfectly clean and felt very cozy. The extra touches of complimentary cinnamon swirl bread, popcorn and much more made for a very relaxing experience. It was great to spend some much needed time away hiking in some of the local parks. Thank you for sharing this wonderful oasis with us Shari
Guest favourite

Apartment in Davis
4.9 out of 5 average rating, 63 reviewsRed Spruce Rental
CarolineRating, 5 stars5 days ago
Mark was a great host! It was a last minute stay and he was very responsive. We had a toddler that made some noise and he was very understanding and friendly as we arrived late and made some noise. Will definitely stay again.

Apartment in Terra Alta
4.7 out of 5 average rating, 122 reviewsLucky Duck * New LIsting*
FrankRating, 5 stars8 months ago
The Lucky Duck is a very calm and relaxing place to stay. We enjoyed the views and the local population of ducks and geese who welcomed us as we came and went. The place was spotless & spacious and had all the little things we needed for a great visit. Would highly recommend booking.
Top Guest favourite

Apartment in Springs
5 out of 5 average rating, 8 reviewsLoft apartment
MorganRating, 5 stars2 days ago
This was probably the nicest and most well organized Air bnb I’ve ever been to. I probably told my partner 30 times in the 2 days we were there that I wished it could be our new apartment.
Top Guest favourite

Apartment in Thomas
4.98 out of 5 average rating, 46 reviewsChuck’s Place, Located on front St. In Thomas
TimRating, 5 stars3 weeks ago
This is a very nice unit in a perfect location. It felt much larger than we expected based on the listing -- it is large for a 2 bedroom place. The front living room/sitting room area was very spacious and has super comfy chairs and couches. Lots of windows and light as well. Kitchen is modern and clean and has all the basics for simple cooking. Location is perfect for seeing Thomas without getting in the car -- coffee shop right downstairs. Lots of hiking options nearby. We will rent it again if we come back to Thomas. Debbie is a great host. Our car battery was dead when we were ready to depart, but she had someone helping us get it started within minutes. Above and beyond helpful.

Apartment in Swanton
4.5 out of 5 average rating, 6 reviewsTo Valhalla II
Daniel GabrielRating, 5 stars1 month ago
Nicole was extremely nice, gave great local recommendations and directions. House was beautifully maintained and had all the amenities we could need. the bed was the most comfortable bed I've spent a night on while out. WiFi code that was provided and super helpful because Verizon counted at roaming in parts of the area. WiFi was also very good. She also provided snacks and baked goods that were amazing. The location was also one of the cheapest stays in the area for what you can get. Couldn't recommend enough! 5 stars across the board!
Apartment rentals with a hot tub
Top Guest favourite

Apartment in Oakland
4.91 out of 5 average rating, 122 reviewsPrivate Unit on Farm with Kitchen & Balcony
NicoleRating, 5 stars3 weeks ago
It was a cute little carriage house apartment. The jetted tub was nice, it had a coffee pot and blackout curtains. Though we didn’t use it, there were EV charging stations and worth noting. It’s about 5 miles from Oakland proper and 10 miles from the touristy part of Deep Creek, so close enough but far away enough. If you are looking for a place to get away with amazing views and to check out from the real world, this is the spot. Kam was responsive when we did message her. Definitely would recommend.

Apartment in McHenry
Splendid dog-friendly home with hot tub, deck
RuthieRating, 5 stars5 months ago
We booked this place last minute for a snowboarding getaway for a rare Maryland powder day! This place is central, located less than 5 minutes from the ski resort and restauraunts in the area. The hot tub after a day on the slopes was a hit. Cozy, had everything we needed. We were plowed out and the walkway was shoveled for us. Low maintenance for visitors! We would definitely book again!

Private room in Oakland
4.57 out of 5 average rating, 7 reviewsOakland Home Efficiency Apartment
LaurenRating, 5 stars44 months ago
An absolutely beautiful location! I was able to watch the leaves change in fall while soaking in the deck hot tub. The studio apartment was perfect as my home away from home while on a travel nursing assignment. I had everything I needed. I was able to bring my roku and watch my TV shows while relaxing in the recliner chair. The shower is very roomy. I love that a washer and dryer was included. The only thing I wish it had was a toaster oven…but that is a luxury not a need. The stove, toaster, and microwave were perfect for my month stay. I highly recommend this place for anyone looking to “get away” or working in nearby by Oakland, MD. The host is wonderful and very responsive.
Top Guest favourite

Apartment in Grantsville
4.98 out of 5 average rating, 124 reviewsYoder School Guest House with wifi and hot tub
LauraRating, 5 stars3 weeks ago
We had a wonderful stay at the Yoder School House. It was so peaceful and relaxing, especially the hot tub with a lovely view of the farmland and watching all the birds at the feeder and in the field over coffee in the mornings. The house had everything we could need - Rhoda is very thoughtful in stocking the kitchen and even leaving fun board games. We loved the proximity to the Casselman Creamery, and it was a great location for day trips to hike Mount Davis and explore Ohiopyle State Park in PA. WE would definitely stay here again! Highly recommend!
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- Seven Springs Mountain Resort
- Fallingwater
- Canaan Valley Resort & Conference Center
- Blackwater Falls State Park
- Timberline Mountain
- Hidden Valley Resort
- Ohiopyle State Park
- Wisp Resort
- Pikewood National Golf Club
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- Lodestone Golf Course
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- Mountain Dragon Mazery Fine Honey Wine
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