The Oaks Waterfront

The Oaks Waterfront Inn in Chesapeake Bay

About this inn

Located in Chesapeake Bay, this attractive inn for $144 per night is a fantastic option for your next vacation. Featuring complimentary WiFi, The Oaks Waterfront offers accommodation in Saint Michaels.

Amenities

Pool

Air conditioner

Kitchen / Kitchenette

Internet / Wifi

Fireplace

Smoking allowed

Parking

Dishwasher

Wheelchair accessible

Garden

Map of Chesapeake Bay, NC

Nearby attractions

Yorktown Battlefield

106.14 miles

American Revolution Museum at Yorktown

The Oaks Waterfront

4.7

Outstanding(162 Reviews)

Inn in Chesapeake Bay, NC

Reasons to book

People love it hereGuests give this property a top rating

Includes essentialsGarden, Pool, Kitchen / Kitchenette and more

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

$$$$

About this inn

Amenities

Pool

Air conditioner

Kitchen / Kitchenette

Internet / Wifi

Fireplace

Smoking allowed

Parking

Dishwasher

Wheelchair accessible

Garden

Map of Chesapeake Bay, NC

Nearby attractions

Yorktown Battlefield

106.14 miles

American Revolution Museum at Yorktown

Reviews

4.7/5.0

Outstanding(162 Reviews)

100% verified reviews

9.0

Aug 2023

St. Michael's, MD Boutique Inn that will exceed your expections!

The breakfast was delicious and the wait staff was attentive. We stayed for several days, so we would've enjoyed more variety in the breakfast menu. The room was cozy and beautifully decorated. The bedding was luxurious and we thoroughly enjoyed relaxing on the dock. The staff, especially Lamond, is polite, professional, and dedicated to providing an exemplary experience.

We would have enjoyed a Keurig in our room. One of us had to get dressed and venture outside of our room each morning to the lobby to grab a morning cup of coffee or tea. Additionally, it would have been great to have a small in-room refrigerator to store some snacks or beverages during our stay. Our stay at The Oaks was during the early part of the week. Unfortunately, their bar is only open Wednesday through the weekend as the venue is largely a wedding venue. The owner happened to be on-site during our stay and was more than willing to provide adult beverages well outside standard hours. We loved seeing Henry, The Oaks Waterfront K9 "fur-bassador." The venue a fantastic St. Michael's boutique inn that couples should not pass up for a romantic weekend away.

9.0

Aug 2023

Quiet retreat but close to restaurants and activities

Beautifully maintained property in a tranquil setting. Very friendly and helpful staff who were attentive to all needs. We had a delightful stay for a weekend.

There was nothing to dislike. Just a suggestion…. they are trying to meld the sometimes competing goals of catering to an event oriented clientele vs a quiet weekend for individuals. To do both is difficult in a venue this size. But as it develops (it is newly renovated) I hope they can tailor the services ( e. g. a small spa would be great on- site) for both groups with the same degree of attention. It has loads of potential….needs a new pool!

10.0

Jul 2023

Our stay was relaxing and totally worth it

Everything was great. The staff went out of their way to make sure everything was good

Nothing

10.0

Jul 2023

Gorgeous facility and location, from the time we arrived to our departure the staff was incredible.

The breakfast was delicious each morning and a great selection. Staff was excellent and attentive.

There was nothing thing I didn’t like!

6.0

Jun 2023

Paid alot of money for short getaway. Not worth the money.

Beautiful, waterfront and impeccably clean. Beautifully decorated . Comfortable bed.

No elevator to third floor with very narrow steep steps. Ice machine not working. Breakfast was just average with coffee being only luke warm. Internet is spotty.

10.0

Jun 2023

Relaxing, and replenishing in beautiful and comfortable surroundings ,inside and outside the hotel.

the room ,view and balcony were extremely comfortable, attractive and pristine. there were so many comfortable spots to sit and relax and enjoy the peaceful and beautiful view.

The breakfast was fine and the service was very good, but the level of the breakfast was not as superior as everything else about the place, in terms of choice and quality.

9.0

May 2023

Intimate, friendly and a beautiful property.

This is a location designed for perfect weddings, and the scenic environment and quality of rooms, buildings are top quality. Only recently opened, it was effectively a B&B, but the lovely staff led by Linda stepped up and made sure that we were comfortable at ALL times, including producing a glass of wine before we we taken off to our dinner reservation by the complimentary town shuttle in to St Michael's. The breakfast was excellent and promises well for bar and dinner options being planned (in time for our next visit?). Coffee was always on tap in the lobby, usually along with some muffins or cookies. It was easy to feel spoiled.

Once the bar and dinner options are fully operational, it will be hard to find any improvements to suggest. Loved our stay.

9.0

Nov 2022

We would definitely go back. Overall, we had a very enjoyable stay.

The staff couldn’t have been more accommodating particularly the woman who served breakfast in the morning. I think she was a manager.

We stayed in the cottage. There were definitely some deferred maintenance items i.e unfunctioning blinds, broken rings on the curtains. The items in the kitchen seemed disorganized. The Wi-Fi signal was poor or non-existent.

10.0

Oct 2022

Excellent, hope to return soon

Customer service, breakfast, and view.

No microwave or refrigerator in room.

10.0

Aug 2022

Very relaxing stay in a quiet area just a short drive to St. Michaels, Easton towns.

Breakfast , peaceful outdoor area

Could use some shade in the pool area

10.0

Aug 2022

Excellent despite work being done on and in the property.

Beautiful property on the water.

Front of property grounds was having major ground work done and building was getting windows replaced. This involved workers throughput the building and

8.0

Aug 2022

relaxing and comfortable

beautiful outdoors

really liked everything

9.0

Aug 2022

It was very relaxing and enjoyable.

Breakfasts were very good and servers very attentive. Our room was was small but well furnished. The cookies and chocolates were a nice touch.

9.0

Jul 2022

it was very nice, and o good value

unpretentious, quiet, great breakfast und courteous staff. the ground are also very lovely.

There weren't enough boats to use. there should also be a couple of paddle boards and maybe a row boat or two.

9.0

Jul 2022

Really enjoyed it. We will be back.

Great breakfast and evening reception!

10.0

Jul 2022

Exceeded my expectations.

Our room was exceptionally spacious with a sizeable balcony out front that I wish we had had more time to take advantage of. The staff was very accommodating and breakfast was a lovely surprise each morning. The property was more beautiful than I could have imagined.

Just that the 3hour and 18min. drive I anticipated (NY to the Oaks) took more than 5 hours. Don't think you can do much about that.

7.0

Jul 2022

Good

Breakfast was good. The amenities like bikes, canoe and shuffleboard were really fun. Sitting by the water with wine in the evenings was great. It's a short drive to St. Michaels.

It's one of the loudest places I have ever stayed. They should give every guest complimentary earplugs. You can make out the conversations of people in other rooms--you can hear when they put down the toilet seat! And our room was next to the deck so anytime someone would go out there the outside door would slam and our door would rattle. Disappointing given the price and otherwise lovely accommodations.

9.0

Jul 2022

The property is beautiful and well appointed. The staff goes above and beyond to ensure you have a great stay. Bonus the

Great views of the water.

All was great!

10.0

Jul 2022

Really enjoyed our stay, quiet, comfortable, beautiful grounds, great breakfast and service.

Views on the property were exceptional. The breakfast was awesome; we would stay there again for sure, thanks!

TV volume max was low, hard to hear with the AC on, no biggie.

10.0

May 2022

Lovely place for a quiet getaway.

Beautiful well kept grounds on a quiet cove. Breakfast was wonderful- several choices of entree and warm scones and muffins. Room was spacious and pretty.

There was a door to the deck just outside our room and other guests allowed it to slam quite often.

10.0

May 2022

Exceptional

It was a great stay - the room was clean, spacious and very comfortable - loved the little cookies too! Staff was very friendly and helpful; the food was a perfect B&B breakfast and the grounds were beautifully kept.

10.0

May 2022

Exceptional

The property was gorgeous, staff was exceedingly friendly and accomodating. They had the best brand of coffee and the breakfast options were delicious.

9.0

May 2022

We had a very enjoyable 2 night stay at this beautiful location.

Lovely breakfast, beautiful view. Friendly and accommodating staff.

Our room was next to a noisy hvac unit and also directly above the kitchen. Numerous coolers were unloaded from a truck trailer after 11 pm on our last night there and it was extremely loud and annoying.

10.0

Feb 2022

Fantastic stay!

Beautiful interior design and spacious cottage. Fantastic breakfast! and wonderfully kind and helpful staff. We will return soon. Highly recommend booking the cottage.

Completely met our expectations in every way.

10.0

Feb 2022

we can’t wait to go back! the staff was great as was the room and the entire venue - and we loved the bedtime cookies!

the property is gorgeous - we enjoyed hanging out in the living room and enjoyed watching the sun come up while sitting on the porch (beautiful even though it was only 27 degrees outside)!

be aware that guests will need to climb steps to get to their rooms

10.0

Feb 2022

A boutique blend of a B&B and a hotel with excellent customer service and location.

The staff was amazing from initial booking until final checkout. The property, common areas, and our room were well maintained and perfect for the style of the house and location. The breakfast was excellent and started each day off right. Location allows easy access to Easton and Saint Michaels. WiFi is very good running multiple devices with no issues.

In room entertainment could use an upgrade, we brought an Apple TV box and streamed content for a better experience.

FAQs

How much does this inn cost compared to others in Chesapeake Bay?

The average price for a rental in Chesapeake Bay is $349 per night. This rental is $205 less expensive than the average.

Is parking included with this inn?

Yes, parking is listed as an amenity at The Oaks Waterfront. For more information, we encourage you to contact the property about where to park.

Is there a pool at this inn?

Yes, a swimming pool is available for use at The Oaks Waterfront. Enjoy the water!

Is The Oaks Waterfront pet friendly?

Unfortunately, this inn is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at The Oaks Waterfront?

We found 11 amenities for this rental. This includes pool, air conditioner, kitchen / kitchenette, internet / wifi, and fireplace.

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The Oaks Waterfront

About this inn

Amenities

Map of Chesapeake Bay, NC

Nearby attractions

The Oaks Waterfront

Inn in Chesapeake Bay, NC

Reasons to book

About this inn

Amenities

Map of Chesapeake Bay, NC

Nearby attractions

Reviews

FAQs

How much does this inn cost compared to others in Chesapeake Bay?

Is parking included with this inn?

Is there a pool at this inn?

Is The Oaks Waterfront pet friendly?

What amenities are available at The Oaks Waterfront?

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