Call to claim the three-night Spring special! 3rd night 1/2 off. Both locations!
Charming Accommodations
At The Oaks Bed & Breakfast - DC/MD, we offer a variety of charming accommodations designed to make your stay comfortable and relaxing. Our rooms are beautifully decorated with a blend of modern amenities and classic touches, ensuring you have everything you need for a restful night's sleep. Whether you prefer an elegant cozy room for one or two or a spacious suite that can accommodate 3-5, we have the perfect option for you.
Annapolis Rental Home
Come experience The Oaks in Annapolis: a distinctive B&B in Historic Downtown, Maryland. Offering renovated suites in a historic home, The Oaks Annapolis blends historic charm with modern luxury. Just a short walk from US Naval Academy, City Dock, Main Street, and Maryland Avenue, enjoy the best of Annapolis's city life in a peaceful residential retreat.
Features include a sitting/game room, dining area, and a living room perfect for entertaining. The second floor has three en-suites, two with full bathrooms and one with a private balcony. The third floor offers two more en-suites, including one with a rooftop deck and two full beds and one with a king bed. There is also a suite with a queen bed. Enjoy the tranquil back patio, an ideal spot for relaxation or gatherings. Don't miss this unique blend of Annapolis history and contemporary elegance and the opportunity to visit, stay and play at the historic Oaks B&B.
Smokey Quartz - King and Queen Beds Two Room Suite and shared bath ($375-$500)
Ruby Red Queen Suite with private portico ($300-$425)
Blue Sapphire Queen Suite with jacuzzi tub ($325)-$450)
Gold Topaz King Suite with jacuzzi tub ($350-$475))
Purple Amethyst Two Full Beds Suite with private rooftop deck ($375-$500)
Emerald Green Queen Suite (no private bath) ($150)
4th floor Kids Loft with 3 twin beds in combination with any of the suites ($150)
You may see the whole house listing here:
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Testimonials
5 Stars
Henry 6/10/2024
I had a wonderful time at Oaks B&B. Sharon and Quinton are very friendly. The B&B was clean, quiet, great location, and the breakfast was excellent Great place to run and exercise in the park and hiking trails. Visited Glenstone Mansion Art Gallery which was nearby. I will stay again.
5 Stars
DeJuan 5/12/2024
Sharon and Q were very friendly and inviting. My entire stay felt like I was visiting family. Breakfast was delicious and filling and it’s hard to top the nightly happy hour after a long day. I highly recommend and definitely will stay there again. Very hard to describe how immaculate and private the room was as well as the property. Sharon and Q have set the bar high for Bed and Breakfasts.
5 Stars
Coco Benitez 10/18/2023
My stay here was a little research and development :) I am a life coach and I host women’s wellness retreats and stayed one evening at The Oaks B&B! I have been on the search for a local place that could accommodate an intimate group setting for my “Beauty & Aging” retreat. After spotting this special B&B gem online, I booked a stay to experience Sharon and Quinton‘s hospitality myself :) Sharon greeted me at the front door with a warm welcoming smile, I signed in and grabbed a fresh baked cookie! After placing my things in the “Rose Respite” room, Sharon took me on a tour so I could see the entire home which I greatly appreciated. My boyfriend joined me later that evening, just in time for wine hour, which was lovely. The room designated for wine time was such a delight and the special tasty treats were a bonus! Sharon really thought of everything! My room had a cozy lighting, all of the details outlined in the amenities were accurate, my bed was incredibly cozy and comfortable and I felt like it was my home. Breakfast was a highlight ,with the smell of coffee and delicious food filling our room had me up early in the morning! Quinton is quite the chef :) We came down at 7:30 am and everything was prepared! I really appreciated how the day before Sharon confirmed what time would be good for breakfast and she easily accommodated. What a special treat, especially the 1 PM checkout time. After chatting with another guest after breakfast, I explored the neighborhood and took a lovely walk, Yoga was fantastic! I later sat on the outdoor patio, and mentally thought through the incredible retreat I am planning for seven amazing women! Sharon and Quinton make you feel at home. What most touched me was the level of comfort and safety I felt. I am a woman of color, so it felt wonderful staying in their home and supporting a black owned business. I can’t wait for my ladies to experience this charming bed-and-breakfast! God willing more retreats at The Oaks Bed & Breakfast to come! Thank you both for making your personal dream a reality so we can all enjoy!
5 Stars
Michelle 3/26/2023
This place is an absolute gem! A beautiful property that is close to town, but also away from it all. The accommodations are comfortable and the hosts are fantastic. Both nights that we were there, we had a great time visiting in the living room with the hosts and other guests. The breakfasts that were provided were better than most restaurants. I'm not joking. The food was wonderful! After visiting The Oaks, other Bed and Breakfast places pale in comparison. It's an excellent place.
5 Stars
Kimberly C. 7/6/2022
The Oaks Bed & Breakfast is a beautiful, clean, and comfortable establishment! I loved my experience there and the owners are professional and extremely accommodating. The house is beautifully decorated, and the grounds are well maintained and welcoming. I can't wait to go back and stay longer!
5 Stars
Charles 5/5/2022
I loved my short stay with Bernard and Sharon! I booked this last minute for a short two-night stay. They were very accommodating and welcoming. I even had to be up and out the door by 5:30am in the morning for an event. I told them I did not need breakfast that morning, however they insisted and had a full-course breakfast for me ready at 5am. MUCH APPRECIATED! Would recommend and stay again!
5 Stars
Duane 2/1/2022
The hosts provided a wonderful experience. The home was beautiful, the room was a great size and had all of the amenities I needed. There was even a special shower body wash for men that smelled great. Lastly, breakfast was amazing. I'll be back again when I'm in the area!
Thank you both for a great experience.
5 Stars
Tryphena E. 10/26/2021
Thank you, Quinton and Sharon Wilder, Esq., for an unforgettable birthday weekend. We were greeted at the Oaks Bed & Breakfast by Sharon Wilder, Esq., with a nice tour and escorted to our cozy bedroom "The Champagne Lounge" which had an assortment of chocolates and bottled water. We were deeply touched with the champagne served in the living room with a charcuterie board and a personal birthday card from the owners before heading to dinner. The evening ended with a nice fireside chat in the serenity garden. We thoroughly enjoyed the proximity to Georgetown and DC. The breakfast was simply delicious! This is truly a hidden gem in Montgomery County, MD. We are very proud of the owners establishing the only Black owned B&B in Montgomery County, MD. Fraternities and Sororities please support!
Clarence Johnson, Jr. and Soror Tryphena Ellis-Johnson
5 Stars
Wendy 9/24/2021
PERFECTION! The location, the rooms, the food, the ambiance, and of course, the hosts. Every room is well designed, comfortable, and with whatever you need readily available. Great for getaway, staycation, groups, or events. Peaceful location with a short ride to downtown Bethesda for shopping and/or dining. This one is a winner
5 Stars
Aisha 1/10/2021
Amazing weekend celebrating my birthday! This was the first time I've stayed at a bed and breakfast. I've avoided them because I'm such an introvert and didn't want to "mix and mingle" with others. Sharon and Quinton were perfect! The best combination of hospitality and giving us space to just relax as well. I truly felt like a guest in a friend's home and not a client frequenting a business. The Rosé Room was beautiful and cozy. I was grateful for the extra blankets in the closet one night when I got chilly and I used one of the masks in the bathroom basket that were available to us. From the wine selection, to the snacks, to the delicious breakfast -- nothing disappointed! The local area was also perfect for our Saturday bike ride. Beautiful and quiet neighborhood, easy to find and not far from shopping and restaurants.
5 Stars
Ebony-Nicole K.1/2/2021
This place is exquisite. I did a four-day marathon dissertation writing retreat here. It was a huge success. I left having finished chapters 1-3. The room I stayed in was perfect (The Rose room). So many little, but beautiful, touches- from the art work to the candles and chocolate. I did my research and wrote daily in one of the cozy and elegant sitting rooms. My backdrop was a warm fireplace and a beautifully lit Christmas tree. I was able to take a walk and enjoy nature in the wooded neighborhood. The hosts, Sharon and Quinton were beyond accommodating and professional. Each morning I was served a five star breakfast and in the early evenings I enjoyed the wine hours. The wine selection is vast. Leaving was difficult. The hosts truly enjoy having and serving their guests and it resonates in all they do. I highly recommend this lovely upscale bed and breakfast. I will be back, for sure. Next time for a romantic getaway. This was my first bed and breakfast experience but not at all my first travel, lodging, or restaurant experience; and I can say without a doubt that I will be back and that others now have a standard that may be hard to beat! I felt so at home in this space and pampered by the proprietors and housekeeper alike! The food was delicious, the ambience was perfect, the neighborhood was refreshing, and the conversations with strangers were priceless!
5 Stars
Erin M. 12/30/2020
I enjoyed both my solitude and the engagement with others that the space afforded me! There was a lovely fire pit out back where I enjoyed a nice whisky and the moon one night. During the day, I was able to enjoy a nice guided run through the neighborhood (with my Peloton app and Airpods). And one evening I even enjoyed some socially distant camaraderie and a television program with the proprietors and another guest in the beautiful family room. I got some great sleep and just the refreshment I needed heading into my law school finals. And truly, the backyard is one of the nicest spaces I've seen, particularly for the amount of space there; they really did so much with the yard and the seating. I especially liked that the fire pit was level with my bedroom. I stayed in the lovely blue room, which I believe is the Zinfandel. The touches were also amazing - from the candles to the lighting options back to the many sweet and salty treats!
Both Inns are available for individual suites and short-term
Luxurious space and accommodations; Consulting, Wellness
Welcome to your home away from home! The Oaks not only offers luxurious accommodations for overnight travelers but we offer event spaces, curated events, and customized retreat packages featuring wellness, nutrition, yoga, and diversity coaching/training. Perfect for small groups seeking to renew or build connection.
Give the gift of travel!
Gift Cards
$300.00
($24.50 shipping)
20% off 3rd night with gift card special!!!
Non-refundable - expires 2 years after purchase.