Get 20% off for the Annapolis special when you book. 202-681-4466
Get 20% off for the Annapolis special when you book. 202-681-4466
Welcome to your home away from home! The Oaks Hospitality Group not only offers luxurious accommodations for overnight travelers but we offer customized retreat packages featuring health, wellness and diversity coaching and training sessions. Perfect for small groups seeking to renew or build connections together!
The Oaks B&B inns are small luxury lodging establishments and exclusive spaces each location has seven guest rooms, instead of the 50 or more found at most inns or hotels. We also offer unique spaces for wellness activities, group coaching, yoga sessions, private retreats and events. As the proprietors, we treat travelers as our invited guests rather than anonymous room numbers. You will be greeted upon arrival where we will provide you with a tour and usher you to your suites. Our guests are treated to lots of little deluxe touches like chocolates on their pillows, baskets of bath and beauty products, luxurious fluffy bath towels, mini-fridges, complimentary high-speed Wi-Fi, and flat screen tv’s in each room. Our en-suites in the Bethesda are aptly named, Rosé Respite, Champagne Lounge, Chardonnay Executive Suite, Zinfandel Zen (with or without the Zen Family Suite), the Riesling Room, and the Cabernet Red are perfect for vacations, golf trips, romantic get-a-ways and bridal showers as well as business travelers and families wanting a home environment.
And, of course, there's the "breakfast" in bed and breakfast, prepared daily that comes with the price of the room and is served each morning in a communal dining room or a private table for two, by reservation, in our well-appointed living room. The Oaks B&B features frosty glasses of iced tea or lemonade on the patio on hot summer afternoons and cups of cocoa or hot cider in front of a cozy fire after neighborhood walks on wintry afternoons. You can come home to plates of fresh-baked cookies in the foyer or enjoy movie nights with popcorn in the comfortable family room. You may choose to chill out and listen to music in the living room, participate in weekly yoga sessions, and enjoy wine and cheese evenings--all as part of the room rate.
We can even arrange the courtyard, terrace and other outdoor spaces for private, exclusive guests, dinners and lawn parties. Please contact us so we can meet your needs!
Conveniently located 5 miles outside of Washington, DC, our guests can easily access the city with its many national parks and museums, shows at the Kennedy Center, The Anthem, Howard Theater and Blues Alley; and the famous Wolf Trap outdoor concert venue in Tyson’s Corner, Virginia is just 15 minutes across the Potomac River. There are plenty of outdoor activities to enjoy - all within a few minutes - including biking on the C&O canal; walking through the Cabin John trail; hiking on the famous Billy Goat trail; kayaking, canoeing and sailing on the Potomac River; dining at world-renowned restaurants and barhopping in Georgetown, sightseeing and, of course, shopping at the famous “City Center”. Westfield Mall is located 5 minutes away. We are a short drive to Glenstone Art Museum in Potomac, MD, and all the Virginia Wineries! Montgomery County is home to Strathmore Hall, Bethesda Blues & Jazz Club, the luxe Pike and Rose, and a local farmers market in downtown Bethesda.
The Oaks is also a short walk or drive to several major golf courses including TPC Avenel, Congressional Country Club, Columbia Country Club, Bethesda Country Club and Kenwood Country Club.
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.
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.
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.
Bernard and Sharon were fantastic hosts! They put a lot of thought into every detail, from the decor to the food and beverage, we were so well taken care of. We had the best anniversary weekend at the Oaks!
Amazed at your attention to detail. The beautiful accommodations, the appetizers, the champagne, the cookies, the breakfast, the hand-written note, etc., etc. Not to mention the friendly conversation! We were honored to be your guests.
Coco Benitez 10/18/2022
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!
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!
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!
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.
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
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!
Sharon goes above & beyond to make your stay feel truly special. The homemade breakfast every morning to the freshly baked cookies in the afternoon are delicious!!! She adds a special touch with her wine & cheese in the evenings and a 1pm checkout time. The property is very spacious and comfortable yet private and homey. We will stay here again!
Ajay G. 5/22/2021
The Oaks is amazing!! I am so glad I chose it for my solo, birthday getaway. My friends stopped by for Wine Hour and didn't want to leave! Sharon and Quinton are very hospitable and gracious with their space. There are several spaces to be alone or gather with others. The rooms are impeccably decorated with so many subtle touches to match the themes. The morning of my birthday, I had breakfast waiting for me. They also gave me a birthday card...HOW THOUGHTFUL! They enforce COVID precautions which is comforting. The Oaks is definitely a home away from home. My friends are already planning their stays there. It was perfect for celebrating my National Holiday! I look forward to going back. Thanks Sharon and Quinton!!
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.
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!
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!
There were also a slew of COVID-19-related health protocols and a form I had to complete about my prior health and whereabouts, plus a temperature check upon arrival for all guests. That made me feel safe for my first lodging experience in the company of others outside of friends or family. I highly recommend!
A. Beckwith 11/20/21
My recent stay at The Oaks in Bethesda, MD was like no other. Upon my arrival, I was greeted by Sharon, the fabulous host, and escorted into main entrance foyer of this unique bed and breakfast. I was immediately offered a refreshing beverage and checked-in. After check-in, Sharon led me on an informative tour of the property and subsequently to my room. As a wine enthusiast, I was ecstatic and excited to stay in the Rose Respite. The room perfectly fit my needs and was so comfortable that I did not miss my own bed during my stay at The Oaks.
Michelle T. 12/4/22
I enjoyed a fantastic and relaxing time away from home. My room was really nice with a private bath with jetted tub and really comfortable bed! The breakfast was delicious, fulfilling and is different every day. It was really great to take my coffee on the front patio and watch the wildlife and birds. It took me exactly 7 minutes to get to DC, which was a great plus. I was even able to print a document that I needed for work! I will be back with friends! Michelle T.
Ask us about the birthday month specials!
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 bedroom suites, two with full bathrooms and one with a private balcony. The third floor offers three more suites, including one with a rooftop deck. 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. You may see the whole house listing here:
Enjoy a complimentary daily breakfast that features a chef's special in addition to assorted breads, pastries, cereal, fruit, juices, cocoa, hot tea and coffee. Vegan and gluten-free options available! The lounge is available in the afternoon for guests to relax with a book, a laptop, tea and coffee, and wine and cheese hour. You may also enjoy our front or back terrace, outdoor firepit, or even reserve space for a lawn party!
We offer a variety of amenities to make your time with us comfortable. We provide complimentary high-speed internet access. You may arrange cooking demonstrations and healthy cooking coaching, wellness and yoga sessions, or life coaching. We can also provide on-site sessions with our massage therapists.
Our outdoor event spaces are available for our guests. Please call us to discuss!
Join us during your birthday month and enjoy birthday month specials including a champagne toast!
Our partner, Reston Limousine works with our winery partners to ensure our customers have the best experience possible on our tours. We cater to clients who want to experience the burgeoning popularity of Northern Virginia wine in beautiful countryside settings.
While we offer weekend public winery trips, customizing your own winery tour allows you to:
Here are some questions to help you get started planning your private winery tour:
Whether this is your first visit, or you have been a guest many times, we want your experience to be excellent. We are available to help with any questions or concerns you may have.
Montgomery County, MD License: BCA-103087
We met when I was 16. I was an incoming freshman, he was a senior. He became the first love of my life and we dated my whole college career. When he graduated, and moved back to Boston, we spent practically every weekend in either Boston, or on campus in Amherst.
Then I graduated and moved to Boston, to be closer to him and to work while waiting to start law school.
I asked him to come to Washington, DC with me but the timing was not right for him to move. Next thing you know, we broke up, met and married others. Life happened and four kids and good careers but we both knew something was missing....
Fast forward to 2019, we both found ourselves single and our mutual friend reconnected us. We had not spoken in 27 years! BAM! The something missing was found .....the loves of each other's life! We (re-)discovered together our mutual love for spending quality time with family, preparing good food, enjoying good wine, entertaining, peace, harmony, beauty, fitness and creating a wonderful, love-filled home environment!
With our kids all grown up, we decided to realize a long-standing dream and begin to build "The Oaks Bed and Breakfast" which we envisioned as a special place where our guests feel welcomed, pampered, and find home away from home. And finally, in midst of the pandemic, we opened our doors in Bethesda, MD, and after 30+ years, married on May 31, 2021!
Two years later, our dream was everything we imagined and more, so we opened a second location in Annapolis, Maryland.
Come join us in celebrating love and life and plan your own get-away with a visit to one of our Oaks' properties!
20% off 3rd night with gift card special!!!
Non-refundable - expires 2 years after purchase.
See for yourself what makes our rooms second-to-none
Double bed, cable television, full private bath
Queen bed, cable television, writing table, private bathroom
Queen bed, full bed, twin trundle beds, 2 cable television, full sofa, full bath with jetted tub. The Family Suite accommodates 5 people with shared bathroom
Queen bed, cable television, full sofa, full bath with jetted tub
Two double beds, convertible sofa, cable television, private bathroom, private dining/meeting space for 4-6 guests, microwave, Keurig machine. featuring a very private, spacious (30x25 ft.), exclusive use of the adjoining ROOF-TOP deck.
Queen bed, sofa, cable television, private bathroom
King bed, cable television, private bathroom
Welcome! BOOK your stay in the DC area today! Also please join our mailing list to receive an invitation to our new location grand opening this fall in historic downtown Annapolis, MD!
Sharon & Quinton