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The Oak and Apple, B&B

208 North Second Street, Oakland, MD 21550
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The Oak and Apple, B&B
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8 Reviews from our TripAdvisor Community

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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (2)
Date | Rating
  • English first
  • Any
English first
  • All months
    (8)
  • Mar-May only
    (3)
  • Jun-Aug only
    (4)
  • Sep-Nov only
    (0)
  • Dec-Feb only
    (1)
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Akron, Ohio
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed July 22, 2015

What a find! For the average person, there aren't many reasons in life why you would ever find yourself in podunk little Oakland, MD, but if you do, this is a first-rate Bed and Breakfast that will make the visit a success, regardless of what brought you into town. The proprietors - a sweet retired couple living their later-in-life dream... More 

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Baltimore, Maryland
Level Contributor
43 reviews
21 hotel reviews
common_n_hotel_reviews_1bd8 25 helpful votes
5 of 5 stars Reviewed March 18, 2014

This lovely B&B is spotlessly clean, very comfortable, and well-appointed. Guests are welcome to relax in the living room (with an atmospheric gas fireplace) or in an upstairs sitting room. There is also a large porch, complete with swing, but it wasn't porch weather when we visited. An upstairs alcove houses a small refrigerator for guests to use, a Keurig... More 

Was this review helpful? Yes 2
Pace, Florida
Level Contributor
4 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed June 23, 2013

Recently on a business trip to Oakland Md I had the opportunity to stay at this beautiful B&B. This house is a by far a must see & stay for anyone who travels to this area. Should you be able to stay one night or a few, you will not be disappointed!!! John & Brenda are truly a remarkable, enjoyable... More 

Was this review helpful? Yes 2
Arlington, Virginia
1 review
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed March 12, 2013

We had a wonderful weekend at Wisp; skiing the trails during the day and staying the weekend at the Oak and Apple B&B. The home is beautiful and John and Brenda are the perfect hosts. Breakfast was delicious and enough to practically skip lunch, even while skiing all day. Local cheese and meats used for the breakfast and the waffles,... More 

Was this review helpful? Yes 2
Arlington, Va
Level Contributor
70 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 38 helpful votes
5 of 5 stars Reviewed August 29, 2012

We had a delightful anniversary weekend at The Oak and Apple B&B. The victorian house sits back on a beautiful treed lot and street. I loved the sound of church bells in the evening breeze. The house and our rooms were comfortable, cozy and well appointed. Brenda and John were knowledgeable hosts recommending weekend activities, especially the stained glass artisit,... More 

Was this review helpful? Yes 2
Virginia
Level Contributor
18 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed February 20, 2012

My husband and I felt at home the minute we walked in the door! In fact, I felt like I was visiting with old friends just from the emails and phone calls to confirm our reservation. John and Brenda have done everything right, from the food to the rooms. The house is beautifully decorated and sits among other gorgeous homes,... More 

Was this review helpful? Yes 3
Annapolis
1 review
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed March 21, 2008

John and Brenda know the real meaning of hospitality. We felt almost like family in our own home. It is apparent that this is simple not just a "business" to them but also a joy. From the detailed welcome to the beautiful and DELICIOUS breakfast everything surpassed our expectations. The location is ideal for the cost and it was worth... More 

Was this review helpful? Yes 6
Washington DC
Level Contributor
4 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
5 of 5 stars Reviewed July 12, 2007

My girlfriend and I stayed at this beautiful Victorian B&B in Oakland, Maryland following a whitewater rafting trip we took on the nearby Upper Youghiogheny River and had a very nice experience. The room was comfortable and clean, and aside from a volunteer fire call in the middle of the night, very quiet. Innkeepers John and Brenda were both friendly... More 

Was this review helpful? Yes 5
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