We are happy to schedule a Virtual Tour of our beautiful event venue via FaceTime or WhatsApp. We will walk you around our private grounds, though the ballroom, and give you a peek at our newly redecorated Bridal Cottage!. The Oaks Waterfront Inn is located in Maryland on a cove off the Chesapeake Bay, just an hour from Annapolis and minutes from St. Michaels, Easton and Oxford.
We offer spacious guest rooms and stunning waterfront event facilities. We are close enough to make your getaway spontaneous, your conference productive, your wedding a joyous gathering of family and friends.
We offer spacious guest rooms and stunning waterfront event facilities. We are close enough to make your getaway spontaneous, your conference productive, your wedding a joyous gathering of family and friends.
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The Oaks Waterfront Inn is the most enchanting of Eastern Shore wedding venues. A country inn tucked back along a winding road set against the backdrop of a quiet cove just off the Chesapeake Bay, The Oaks is a picture perfect setting for a Maryland waterfront wedding. Surrounded by 10 acres of scenic Maryland landscape and waterfront, The Oaks Waterfront Inn sets the perfect ambience for your celebrated occasion. When your world closes in on you, plot an escape to ours. Pack up and leave on a whim.
The well-appointed waterfront inn rooms and cottages at The Oaks offer romantic luxury and exceptional comfort. We also fulfill every need with thoughtful amenities and attentive service. Do as little or as much as you would like. For instance, you can relax on our Adirondack chairs and take it all in from a private veranda, or wander the lush grounds.
The setting is magical. And entirely yours. The Oaks Waterfront Inn and its grounds become a private preserve for you, your wedding party, and guests. It's all yours on the evening before, the day of, and the morning after your waterfront wedding. The beautifully landscaped grounds of The Oaks offer a wide variety of outdoor activities in a relaxing setting.
Off-site conferences, fundraising events, or corporate retreats are by definition all business. When it comes to the details of your gathering, so are we. Our picturesque conference event space, numerous breakout locations and unlimited outdoor space create a perfect environment to fulfill your agenda.
Reviews (27)
Maxine Bickerstaff
May 26, 2022
Keirsten MacLellan
May 26, 2022
Beautiful place. They say they aren't in Easton and advertise they are in St Michaels which is false. Even the confirmation email said "We are not in Easton". Really do some digging if you decide to stay there. False advertising and is not at all what we expected for a quick getaway. There is nothing around or within walking distance. Partially our fault for not doing a whole lot of digging and trusting what they advertise on sites.
Alejandra Becerra
Feb 24, 2022
What a beautiful place. The hospitality of the personal is so good. They are so gentle. The breakfast is delicious, and the service is clean. The view is beautiful and the color of the mornings is beautiful. The rooms are big, spacious, they gave you all the implements for the bath. ( high quality), the have chimneys in the rooms and bathtubs. What a pretty place.
Ashley Allen
Jan 07, 2022
Courtney Smulovitz
Dec 20, 2021
The Oaks Waterfront Inn is the absolute perfect wedding venue! We fell in love with it the second we walked in! The property is beautiful and the staff is so kind! We were able to take so many nice pictures on the water, in front of the Inn, and in front of their barns. It really meant a lot to us to have all of our family stay on property the entire weekend!
We had our rehearsal dinner on the dock and it couldn't have been more perfect. We got married in August, but there was a very nice breeze from the water. On our wedding day, Candi couldn't have been more helpful! She checked in several times to make sure we have everything we needed and ensured everything was set up to our liking. Candi and the entire staff were so helpful and couldn't have been any happier for us!
They took the time to get to know us and not just treat us like guests, but family! We loved everything about The Oaks Waterfront Inn and will absolutely be back, multiple times!
We had our rehearsal dinner on the dock and it couldn't have been more perfect. We got married in August, but there was a very nice breeze from the water. On our wedding day, Candi couldn't have been more helpful! She checked in several times to make sure we have everything we needed and ensured everything was set up to our liking. Candi and the entire staff were so helpful and couldn't have been any happier for us!
They took the time to get to know us and not just treat us like guests, but family! We loved everything about The Oaks Waterfront Inn and will absolutely be back, multiple times!
Kathleen Nowell
Nov 19, 2021
Perfect place for a wedding! The Oaks was the first and only venue that my husband and I toured. Tucked away on a peaceful cove, it had everything we wanted and so much more. It's big enough to accommodate our family and friends so that we were able to spend extra time with them, but small enough that the staff could take amazing care of us. Attentive service, delicious food, not to mention the gorgeous views from every spot on the property. We will definitely be back for weekend getaways!
Clarence Lewis
Aug 29, 2021
Great location on the water. Very friendly accommodating staff. Excellent complimentary breakfast. My accommodations were on the top floor was very comfortable & clean with water and front views, and a private deck facing the creek. Price are reasonable. I'd definitely stay again. The entire facility was well maintained and clean.
Maryanne Forte
Aug 18, 2021
Beautiful old inn on the Oak Creek minutes away from St. Michael's. The setting is very pretty - Adirondack chairs facing the creek - a perfect place for reading, coffee, chatting. There is a canoe to take out on the creek and bicycles/helmets available for exploring the area. Nothing fancy - but definitely serviceable! The rooms were very clean - not over-the-top fancy, but comfortable and had everything we needed. Delicious cookies were left in the room when cleaned. Coffee, tea, soda and water are available 24/7. Breakfasts were delicious - choice of 3 options and were prepared and presented wonderfully. Staff was attentive and friendly. Would definitely recommend - this was our second visit in 3 years and we hope to make it a yearly visit.
Gina Johnson
Jun 20, 2021
Johan Spijker
Jun 07, 2021
Very lovely place on the water with owners on property who help ensure a gracious stay. Wonderful breakfasts, very special smoothies and helpful hints from staff for those of us from out of town. Can't imagine a more special spot for our 48th anniversary. Thanks all for a great stay and would very highly recommend.
Erin Ruddy
Jun 04, 2021
Perfect romantic getaway! My fiance and I stayed this past weekend and were blown away by the quiet, peaceful place and service. You can tell that the staff truly takes a lot of pride in this beautiful inn. The breakfast each morning was the perfect amount of food and delicious. We really enjoyed the complimentary canoes on site as well as the Adirondack chairs overlooking the water.
Our room very clean and had a good size bathroom. We loved that we had a gas fireplace in the bedroom! The quaint town of St. Michael's was a short 5 minute drive away. Highly recommend!
Our room very clean and had a good size bathroom. We loved that we had a gas fireplace in the bedroom! The quaint town of St. Michael's was a short 5 minute drive away. Highly recommend!
Catherine Price
Apr 14, 2021
The Oaks was a wonderful place to stay. The staff was very welcoming and helpful. The room was warm and inviting and very comfortable. It was a pleasant surprise to find the bathroom so modern and large as the Inn dated back to mid 1700's. Breakfast was outstanding. Anyone would be greatly surprised at the outstanding experience of staying at The Oaks Waterfront Inn!
Kaitlyn S.
Feb 03, 2021
The Oaks goes beyond a wedding venue. This place is a home for the most memorable and important weekend of your life! Every single person involved goes above and beyond to make sure the bride and groom, plus family and friends are well taken care of. The food is phenomenal, service is perfection, atmosphere is incredible. Everything is immaculate.
My husband and I and our families cannot thank this venue enough, during a time of unknown and a pandemic they worked endlessly with us to make our entire weekend unforgettable. It was better than I ever imagine and the butterflies will last a lifetime. You need to check this venue out! Tracey, Candy, Katie, missy (& everyone!) are insanely generous and kindhearted people. Forever grateful.
My husband and I and our families cannot thank this venue enough, during a time of unknown and a pandemic they worked endlessly with us to make our entire weekend unforgettable. It was better than I ever imagine and the butterflies will last a lifetime. You need to check this venue out! Tracey, Candy, Katie, missy (& everyone!) are insanely generous and kindhearted people. Forever grateful.
Debbie Billings
Nov 17, 2020
Wow! I can't believe that last review! A friend and I just stayed there this week. We were so impressed. Our room was spacious and spotlessly clean. The setting was so peaceful and serene. We loved sitting on the deck looking out over the beautiful waterfront. Breakfast was delicious. It started with a strawberry, banana, basil Smoothie. Then, a mini blueberry muffin and biscuit.
We had a choice of a mushroom omelet or a Belgium waffle with fruit. Both came with sausage. The breakfast menu changes daily. The weather was hot so we spent a lot of time in the pool! We thoroughly enjoyed our stay and can't wait to go back!
We had a choice of a mushroom omelet or a Belgium waffle with fruit. Both came with sausage. The breakfast menu changes daily. The weather was hot so we spent a lot of time in the pool! We thoroughly enjoyed our stay and can't wait to go back!
Shannon W.
Nov 20, 2019
My husband and I married here in June 2019 and we had a wonderful experience! We did a Sunday wedding, which was much more reasonable for our modest budget. Everything went smooth and I have to say the attention to detail there is fantastic! It's a beautiful venue on its own, and you really don't need to add much. The food for the wedding was amazing and the breakfast the next morning is a nice touch.
My only complaint was how short our reception felt. I wish we could have extended it longer (this comes at a price), but it was also discouraged. Likely, because it was a Sunday wedding and there are noise restrictions with neighbors. Overall though, it was beautiful and I couldn't imagine getting married anywhere else!
My only complaint was how short our reception felt. I wish we could have extended it longer (this comes at a price), but it was also discouraged. Likely, because it was a Sunday wedding and there are noise restrictions with neighbors. Overall though, it was beautiful and I couldn't imagine getting married anywhere else!
Amy M.
Jul 10, 2019
My husband and i took a trip to St Micheal 's for our Anniversary. We had a wonderful time at Oak Waterfront Inn. Our visit to the inn was wonderful. The staff were very friendly. They had bikes and canoes to use. We enjoyed the pool and grounds. Our room had plenty of space. It was a short drive to the town of St. Micheal. All the bed and breakfast we saw in town were tiny with little space. Our breakfast each morning was amazing. I would return to the inn just for breakfast.
Win S.
Feb 27, 2019
Gorgeous venue! Stayed here over a holiday weekend in the wintertime and it was quiet, serene and practically empty! (just 2 other parties). I'd love to come back when it's warmer and experience this beautiful place when the temperatures are right to enjoy the outdoors. They have their own dock (so pretty! there are chairs to sit and relax) and a private patio space. There's also a side, private cottage that can be rented out that features a kitchenette and spa tub next to the main inn.
I reserved a King bedroom in the main inn; I made a point to ask for one of the rooms that faced the waterfront area. The receptionist also generously honored and price matched the cost that I saw on Booking.com the day before! Loved the view from my room! The furniture is old English countryside and quaint. Not my usual taste, but it fit this inn's style.
It seems like the place was renovated not that long ago, too. Our room also came with a mini fire place that you can turn on and off. So cozy! I was hoping for a bigger tub in the bathroom, but it was a regular shower + a slight minus that the bathroom was in older condition. The inn-keeper was very friendly and welcoming, making sure that we were doing well and was quick to offer advice (told us what to do in the town and where to shop and eat).
We took his advice and tried the Talbots restaurant, which was excellent! In the common areas, they offer sugar cookies in the late afternoon. I didn't get to try them because we were late to come back after dinner. They also have a communal mini fridge in the living area where you can enjoy complimentary wine, beer or soda! What a nice touch!
Breakfast is served at 9 a.m. on the house. That was my favorite experience at the inn! We ordered the omelet and French toast. They were perfectly cooked with gorgeous presentation. We also had an appetizer of a fruit cup with freshly cut strawberries and a tarragon sprig to top it off (who knew that tarragon would go so well with fruit!) The lighting in the dining room was exquisite.
It would be a cute venue for a special event like a wedding. Apparently, they host about 42 weddings a year - so busy! So make sure you come on a weekend where there's not one.
I reserved a King bedroom in the main inn; I made a point to ask for one of the rooms that faced the waterfront area. The receptionist also generously honored and price matched the cost that I saw on Booking.com the day before! Loved the view from my room! The furniture is old English countryside and quaint. Not my usual taste, but it fit this inn's style.
It seems like the place was renovated not that long ago, too. Our room also came with a mini fire place that you can turn on and off. So cozy! I was hoping for a bigger tub in the bathroom, but it was a regular shower + a slight minus that the bathroom was in older condition. The inn-keeper was very friendly and welcoming, making sure that we were doing well and was quick to offer advice (told us what to do in the town and where to shop and eat).
We took his advice and tried the Talbots restaurant, which was excellent! In the common areas, they offer sugar cookies in the late afternoon. I didn't get to try them because we were late to come back after dinner. They also have a communal mini fridge in the living area where you can enjoy complimentary wine, beer or soda! What a nice touch!
Breakfast is served at 9 a.m. on the house. That was my favorite experience at the inn! We ordered the omelet and French toast. They were perfectly cooked with gorgeous presentation. We also had an appetizer of a fruit cup with freshly cut strawberries and a tarragon sprig to top it off (who knew that tarragon would go so well with fruit!) The lighting in the dining room was exquisite.
It would be a cute venue for a special event like a wedding. Apparently, they host about 42 weddings a year - so busy! So make sure you come on a weekend where there's not one.
Erik M.
Jan 18, 2018
30 years ago I got my first job washing dishes and bussing tables at "The Pasadena Inn", now "The Oaks". I worked a couple summers at this idyllic location and made some great memories. Fast forward 28 years, I stayed at the Oaks for my sister's wedding. While so many things have not changed, a great deal more has only gotten better. The service was friendly, the accommodations quaint, the food very good and the general state of the establishment excellent. Congrats to the owner of the Oaks.
R. P.
Nov 03, 2017
I will say that my lady and I did a one day get away to The Oaks and we had gotten the Cottage House, it was so nice and quaint that I will highly recommend this place it's within 10-15 yards from the water you have privacy what more can you ask for and the staff is wonderful! Perfect getaway for couples and water lovers like me, I will definitely be coming back!
John P.
Aug 22, 2017
DO NOT STAY HERE FOR YOUR WEDDING! This hotel would fit right in with the town of Footloose, because apparently having a good time gave the management cause to be as unaccommodating as people could be. Let me count the ways: 1. They were rude to the bride. Strike 3. I am pretty sure rule number 1 when "serving" as a wedding destination is DON'T BE RUDE TO THE BRIDE.
Be rude to everyone and anyone else (I guess?), but not being rude to the bride is day 1 basics. This alone should make you look elsewhere for your wedding. 2. They were rude to bride's mother. Honestly people if rule 1 is don't be rude to the bride this is clearly rule 2. So, The Oaks managed to drop the ball on the 2 most basic and widely excepted rules of being a wedding destination.and the list is just getting started. 3.
They double booked the bridal suite. Morning after the wedding the bride and groom were told they had not reserved an extra day.even with the confirmation in hand. Even having been proven they were wrong management dared to say they were going to bill the groom. Upon correction, they realized their error. 4. There was no running water.the day of the wedding. That's not fair, water dribbled out of the faucet.and it was ice cold. 5.
They took our beer. What are we, in high school? They threw some non-sense about how they can be the only ones to serve us booze.but clearly this was a reaction to our "making a mess" at the rehearsal. I put making a mess in quotes because a few solo cups were all I saw, but management sure made a big deal about it. 6. The pool was opened late the morning of the wedding.and not at all the day after.
Why list having a pool as an accommodation if you are going to put "chemicals in it" every day right before you're supposed to open it? (Again, their words.) I can actually answer my own question.its cause the pool was lame. Their answer."the rain really messed it up?".What?!? 7. We needed an extra bed for our room. Again, this was seen as some huge inconvenience and took an extra day to get the air mattress. 8.
Other people being shown around the venue while our event was still going on. (Including snide remarks in front of guests.) The list goes on, but you get the idea. Now I know what you may be thinking, some of these things may seem petty or have had legit excuses, but truthfully everything would have been so much better and so much more tolerable if the management had made ANY EFFORT to be apologetic or sympathetic in any of these situations (barring 1-3).
But no, at every turn they were rude, unapologetic and acted as if we were somehow inconveniencing them in some way. You can't argue with the location, the spot is gorgeous, but I assure you there are equally beautiful locations in St. Michaels and will be exceedingly more accommodating. If you do decide to risk staying at the Oaks I wish you the best and hope you have a crowd like ours that can overcome the wet blanket that was the management and power through to have a good time.
Be rude to everyone and anyone else (I guess?), but not being rude to the bride is day 1 basics. This alone should make you look elsewhere for your wedding. 2. They were rude to bride's mother. Honestly people if rule 1 is don't be rude to the bride this is clearly rule 2. So, The Oaks managed to drop the ball on the 2 most basic and widely excepted rules of being a wedding destination.and the list is just getting started. 3.
They double booked the bridal suite. Morning after the wedding the bride and groom were told they had not reserved an extra day.even with the confirmation in hand. Even having been proven they were wrong management dared to say they were going to bill the groom. Upon correction, they realized their error. 4. There was no running water.the day of the wedding. That's not fair, water dribbled out of the faucet.and it was ice cold. 5.
They took our beer. What are we, in high school? They threw some non-sense about how they can be the only ones to serve us booze.but clearly this was a reaction to our "making a mess" at the rehearsal. I put making a mess in quotes because a few solo cups were all I saw, but management sure made a big deal about it. 6. The pool was opened late the morning of the wedding.and not at all the day after.
Why list having a pool as an accommodation if you are going to put "chemicals in it" every day right before you're supposed to open it? (Again, their words.) I can actually answer my own question.its cause the pool was lame. Their answer."the rain really messed it up?".What?!? 7. We needed an extra bed for our room. Again, this was seen as some huge inconvenience and took an extra day to get the air mattress. 8.
Other people being shown around the venue while our event was still going on. (Including snide remarks in front of guests.) The list goes on, but you get the idea. Now I know what you may be thinking, some of these things may seem petty or have had legit excuses, but truthfully everything would have been so much better and so much more tolerable if the management had made ANY EFFORT to be apologetic or sympathetic in any of these situations (barring 1-3).
But no, at every turn they were rude, unapologetic and acted as if we were somehow inconveniencing them in some way. You can't argue with the location, the spot is gorgeous, but I assure you there are equally beautiful locations in St. Michaels and will be exceedingly more accommodating. If you do decide to risk staying at the Oaks I wish you the best and hope you have a crowd like ours that can overcome the wet blanket that was the management and power through to have a good time.
Ted H.
Nov 05, 2015
Outdated. Outdated. Outdated. Getting the picture? A serious reinvestment by the ownership is needed. Im not saying there needs to be a travertine 22 head shower with a flatscreen in every room but clean, undamaged period correct furnishings would be better than current. Staff upgrades are overdue as well. Reading previous reviews we concur that brash, overbearing 'cranky great-aunt from out of town' types that feel an obligation to delve well past the normal reminders about policy and courtesy didnt help the check in or out.
Fresh faces and pleasant greetings would be better recieved. Beautiful location in truly one of the most picturesque places ive ever been and worth serious consideration if in the area on a budget.
Fresh faces and pleasant greetings would be better recieved. Beautiful location in truly one of the most picturesque places ive ever been and worth serious consideration if in the area on a budget.
Caroline V.
Apr 16, 2014
I attended a wedding here this past weekend. The scene was perfect, the good was tasty, and the service was excellent. I specifically wanted to highlight and thank a young server who at the end of the evening noticed I had lost an earring. As I was leaving she found my earring and located me as I was walking out the door. I was so happy she found the earring and was able to find me! Thank you! That is an example of excellent service.
Kelly S.
Nov 10, 2013
If you want your guests, bridal party, and vendors (dj, photog) to be treated like children, this is the place for you. If you enjoy dealing with rude management, this is the place for you. Prepared to be bossed around by the staff. The food was good. And the scenery is nice, but the service just ruins the experience. Ive been here for 4 weddings over the years and have seen the same thing each time. Rude servers and especially bitchy attitude from the management. I recommend you explore other options if you're looking for a nice place to have a wedding.
Buzz B.
Nov 18, 2012
Our daughter's wedding was at The Oaks this weekend. This was a wonderful location for a wedding. It was really neat to have the entire location booked with family and friends. It made the weekend feel like it was our own personal resort. Our room was large, clean and had a great view of the water. When we were ready for shopping, downtown St. Michaels was only 3.5 miles away.
The town had plenty of bars, restaurants, and shops. For the wedding, a family room is provided for lounging during the day and served as an area for everyone to check in periodically. The organization of the guests arriving, hot coca with schnapps, moving to the wedding service on the dock, to the cocktail reception and to the dinner was smoothly handled. The dinner was outstanding. The service was remarkable. I would definitely recommend this location for a wedding.
The town had plenty of bars, restaurants, and shops. For the wedding, a family room is provided for lounging during the day and served as an area for everyone to check in periodically. The organization of the guests arriving, hot coca with schnapps, moving to the wedding service on the dock, to the cocktail reception and to the dinner was smoothly handled. The dinner was outstanding. The service was remarkable. I would definitely recommend this location for a wedding.
Christina G.
Aug 27, 2012
Not great for an outdoor wedding if it might rain. I attended a wedding ceremony that was held under the covered dock. We sat in the back and couldn't see or hear everything. There was also rain, wind, thunder and lightning! Not pleasant. The one AWESOME thing was the meal served for dinner. (I posted a photo on Yelp) it was a Maryland Crabcake that was leaning against a perfectly cooked medium-rare steak that was topped with sauteed shiitake mushroom caps. Underneath the steak and Crabcake were freshly cooked green beans (huge difference if you normally eat yours from a can).
There were also small round, peeled potatoes evenly spaced around the plate. The best part was the creamy and buttery, with a hint of salt, oyster sauce that everything was sitting in. No oyster taste though. SO DELICIOUS! I want to eat that meal every day for the rest of my life.
There were also small round, peeled potatoes evenly spaced around the plate. The best part was the creamy and buttery, with a hint of salt, oyster sauce that everything was sitting in. No oyster taste though. SO DELICIOUS! I want to eat that meal every day for the rest of my life.
Anthony C.
Jun 29, 2012
Everything was great on our two night stay. This inn hosts weddings most spring/summer weekends. But from Tuesday to Thursday you can get a great room at a very reasonable rate. It is about 5 miles outside St. Michaels shopping, and on the way to the Oxford ferry. It is an inn, not a hotel, so you might expect to hear other guests in the hall, etc.
Our room was nice--not the most up-to date in terms of appointments, but very comfortable. The grounds are wonderful. The inn sits on a "creek" which is more like a lake or river. The "creek" flows into the inlet around St. Michaels which flows into the bay. There are lots of adirondack chairs to enjoy the setting, a small pool, shuffle board, etc. A night in the inn includes breakfast, which was nothing short of great. Filling, but not too much, and perfectly prepared. We will definitely return.
Our room was nice--not the most up-to date in terms of appointments, but very comfortable. The grounds are wonderful. The inn sits on a "creek" which is more like a lake or river. The "creek" flows into the inlet around St. Michaels which flows into the bay. There are lots of adirondack chairs to enjoy the setting, a small pool, shuffle board, etc. A night in the inn includes breakfast, which was nothing short of great. Filling, but not too much, and perfectly prepared. We will definitely return.
Alyse R.
Aug 17, 2010
My sister got married at The Oak's this summer. The venue was beautiful, but the management was a nightmare to work with. Approximately 5-10 minutes after the rehearsal dinner ended they turned the lights out on the remaining guests. My sister only saw the wedding coordinator ONCE the entire day. My grandmother and step-mom's flowers went missing for the ceremony.
The reception ended at 10:00 pm and at 10:02 pm they were vacuuming, cleaning off tables, and trying to get us out of there. During the reception my sister had setup a cigar bar for all the men to smoke. A number of the guests were outside smoking cigars and as soon as the clock struck 10 they turned the lights out on them!
The reception ended at 10:00 pm and at 10:02 pm they were vacuuming, cleaning off tables, and trying to get us out of there. During the reception my sister had setup a cigar bar for all the men to smoke. A number of the guests were outside smoking cigars and as soon as the clock struck 10 they turned the lights out on them!