The Oaks Waterfront

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

Deluxe Room, 1 Queen Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

Premium bedding, iron/ironing board, free WiFi, bed sheets

Free toiletries, hair dryer, bathrobes, heated floors

9.8

Outstanding(56 Reviews)

Bed and Breakfast in Chesapeake Bay, NC

4-Star Hotel

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valuePrice for this property is higher than average in the area

Includes essentialsGarden, Pool, Air conditioner and more

About this bed and breakfast

Waterfront bed & breakfast with free breakfast and a rooftop terrace
A rooftop terrace, spa services, and a seasonal outdoor pool are available at this smoke-free bed & breakfast. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a business center, concierge services, and a 24-hour front desk.
The Oaks Waterfront offers 15 accommodations with complimentary bottled water and bathrobes. Beds feature premium bedding. Smart televisions come with digital channels.

Bathrooms include complimentary toiletries and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is provided daily.

Recreational amenities at the bed & breakfast include a seasonal outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Amenities

Pool

Air conditioner

Internet / Wifi

Parking

Hot tub or spa

Garden

Map of Chesapeake Bay, NC

Nearby attractions

Yorktown Battlefield

106.1 mi

American Revolution Museum at Yorktown

Available Rooms

Deluxe Room, 1 Queen Bed

1 Queen

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Deluxe Room, 1 King Bed, Accessible

1 King

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Luxury Suite, 1 Bedroom, Balcony

1 King • 1 Sofa

Sleeps 4

You'll be directed to Expedia.com for availability & pricing

Junior Suite, 1 King Bed with Sofa bed

1 King • 1 Sofa

Sleeps 4

You'll be directed to Expedia.com for availability & pricing

Luxury Cottage, 1 Bedroom, Kitchen, River View

1 King

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

$$$$

The Oaks Waterfront

$$$$

9.8

Outstanding(56 Reviews)

Bed and Breakfast in Chesapeake Bay, NC

4-Star Hotel

Reasons to book

Guests love it hereGuests give this property a top rating

High-end valuePrice for this property is higher than average in the area

Includes essentialsGarden, Pool, Air conditioner and more

About this bed and breakfast

Bathrooms include complimentary toiletries and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is provided daily.

Recreational amenities at the bed & breakfast include a seasonal outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Amenities

Pool

Air conditioner

Internet / Wifi

Parking

Hot tub or spa

Garden

Map of Chesapeake Bay, NC

Nearby attractions

Yorktown Battlefield

106.1 mi

American Revolution Museum at Yorktown

Available Rooms

Deluxe Room, 1 Queen Bed

1 Queen

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Deluxe Room, 1 King Bed, Accessible

1 King

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Luxury Suite, 1 Bedroom, Balcony

1 King • 1 Sofa

Sleeps 4

You'll be directed to Expedia.com for availability & pricing

Junior Suite, 1 King Bed with Sofa bed

1 King • 1 Sofa

Sleeps 4

You'll be directed to Expedia.com for availability & pricing

Luxury Cottage, 1 Bedroom, Kitchen, River View

1 King

Sleeps 2

You'll be directed to Expedia.com for availability & pricing

Reviews

9.8

Outstanding(56 Reviews)

10.0

Sep 2024

Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water pool. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience.

10.0

Sep 2024

Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!

10.0

Jun 2024

Everything was outstanding. We will be back.

10.0

May 2024

The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.

10.0

May 2024

Where to begin with this amazing stay? My husband and I went for a weekend to run the St. Michaels half marathon. We were looking for a quiet, relaxing place and the Oaks Waterfront surpassed our expectations. The property is impeccably maintained and, Linda, made us special early breakfast bags for the race since we would have to leave at 5AM, before breakfast service. She helped us find restaurants, get dinners, it was incredible. The property is so beautiful. We didn't bring our children but it would be a great place for them too!

10.0

May 2024

10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.

10.0

May 2024

Beautiful facility and grounds and friendly staff.

10.0

Apr 2024

Beautiful property, loved it!

10.0

Apr 2024

Beautiful newly renovated picturesque place, we had a great weekend stay. It’s conveniently located close to Saint Michael and Easton downtown close to great food options, museums and shopping. Staff is attentive unobtrusive and Linda deserves a special mention for excellent recommendations for food and things to do. You can see Oaks is a great wedding venue with pretty interiors and exteriors and we were lucky to have a quiet weekend before it’s unavailable with weddings booked for the entire year. Want to especially mention the delicious breakfast and service every morning. We had a lovely stay and found lots of things to do close by. Highly recommend especially if looking for a top notch bed and breakfast experience with pretty deluxe touches all around.

10.0

Mar 2024

Wonderful place. Beautiful. Staff was top notch. Accommodations were outstanding.

10.0

Mar 2024

Exquisite and gracious service. Stunning appointments throughout. Just beautiful.

10.0

Feb 2024

Outstanding boutique hotel on the water. Everything is new. Staff is fantastic. Lovely romantic weekend there

10.0

Sep 2023

Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!

10.0

Aug 2023

Can not say enough wonderful things.

10.0

Aug 2023

Beautiful property, great service, wonderful breakfast.

5.0

Aug 2023

Our stay at the Oaks at Waterfront was wonderful. The hotel has gone through a major renovation and is absolutely beautiful. The staff were so helpful and friendly. No hesitation that we are coming back for another visit. Stay in this little gem of a inn in the St Michael’s area.

5.0

Jul 2023

I would give this property and staff a 12 if ratings went that high.

10.0

Jul 2023

The property is very well maintained, staff is super friendly and property is newly renovated

10.0

Jul 2023

We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!

10.0

Jun 2023

A beautiful property! A beautiful staff running the property! Delicious and Serene. It was a perfect get away!

5.0

Jun 2023

Our visit was exceptional and the hotel was magnificent. One disappointment was we had asked for a king bed and was given two queen beds instead.

8.0

Jun 2023

The property was recently renovated and is absolutely beautiful and relaxing. I think more eating and drinking options on the property would be helpful. The bar wasn’t really open and the only food option is breakfast at 8:30 am. You must leave the property and drive to town for all your drinks and meals which felt like a hassle sometimes.

5.0

Sep 2022

Beautiful Rooms and scenery. Staff very personable and attention to detail lends that personal touch to your stay.

5.0

Sep 2019

The absolute best. Beautiful surroundings, a room facing the water. The small town home atmosphere with seafood and other restaurants on the waterfront. The staff were friendly, helpful and accommodating. I will definitely visit again. I even told my friends!

5.0

Sep 2019

5.0

Jul 2019

A fantastic weekend get away. Upgraded to “The Cottage” . It was very private and quite romantic. The grounds were nice and a short trip to downtown St. Michaels.

5.0

Oct 2018

Beautiful setting on Oak Creek. Only two hours from Ocean City and St. Micheals offers a large variety of restaurants. We absolutely loved our time at The Oaks.

5.0

Sep 2018

Small B & B with waterfront view and friendly staff..........would stay there again

5.0

Jul 2018

Awesome hotel. Great value for the price. I was very pleased and would use this hotel again with no reservations.

5.0

Jul 2018

We really enjoyed staying at this Inn. Its on the waterfront and there are bikes and canoes available for use. Close to St. Michaels, although not walking distance. (about three miles). Changes I would recommend in the room is some kind of shelving unit (wall or otherwise) to put your toiletries, a better hair dryer and extra towels for two people. Breakfast was excellent and cooked to order. The staff was fantastic!

5.0

Jul 2018

We really enjoyed staying at this Inn. It's on the waterfront and there are bikes and canoes available for use. Close to St. Michaels, although not walking distance. (about three miles). Changes I would recommend in the room is some kind of shelving unit (wall or otherwise) to put your toiletries, a better hair dryer and extra towels for two people. Breakfast was excellent and cooked to order. The staff was fantastic!

5.0

Jun 2018

If I could of stayed longer I would have. The breakfast was wonderful and the grounds were great

2.5

Jun 2018

If I could of stayed longer I would have. The breakfast was wonderful and the grounds were great

5.0

Jun 2018

Beautiful views. Love this place.

5.0

May 2018

This was our fourth stay in a B&B on the Maryland Eastern Shore and the best one so far. Very attentive staff and nice toys (canoe, bike) to play with.

5.0

Nov 2017

Our stay at The Oaks was lovely! we were only there for a short stay, but it was so nice that we would have stayed longer had we not had obligations at home. The check-in service was efficient and welcoming, our room was delightful, and the setting and the amenities were just beautiful!

5.0

Oct 2017

I have stayed before and LOVED it. This was no exception.. except the room. This time we stayed in room 20. It was directly above the front door and porch. I could hear everything in the lobby.. door opening and closing, and the front porch lights were a beacon directly into our room all evening. I will definitely NOT stay in this room again.. but I really do LOVE this place.

5.0

Oct 2017

4.0

Sep 2017

The chef/owner oversees every inch the facility and your stay. If you are looking for a peaceful stay in the St Michaels area check out the Oaks.

5.0

Aug 2017

The inn was quite lovely. Each morning a delightful breakfast was available and in the late afternoon cookies were set out. It's right on the water and so peaceful. Also only 5-10 minutes from St. Michael. We thoroughly enjoyed our stay.

FAQs

How much does this bed and breakfast cost compared to others in Chesapeake Bay?

The average price for a rental in Chesapeake Bay is $236 per night. This rental is $203 above the average.

Is parking included with this bed and breakfast?

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 bed and breakfast?

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

Is The Oaks Waterfront pet friendly?

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

What amenities are available at The Oaks Waterfront?

We found 7 amenities for this rental. This includes pool, air conditioner, internet / wifi, parking, and hot tub or spa.

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9.0

Excellent(1 Review)

2 blocks to CNU-5 bedroom house with First floor Master

Villa

in Newport News

Garden · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Chesapeake Bay? Look no further than our Villa, 2 blocks to CNU-5 bedroom house with First floor Master. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$

The Oaks Waterfront

Bed and Breakfast in Chesapeake Bay, NC

Reasons to book

About this bed and breakfast

Amenities

Map of Chesapeake Bay, NC

Nearby attractions

Available Rooms

Deluxe Room, 1 Queen Bed

Deluxe Room, 1 King Bed, Accessible

Luxury Suite, 1 Bedroom, Balcony

Junior Suite, 1 King Bed with Sofa bed

Luxury Cottage, 1 Bedroom, Kitchen, River View

The Oaks Waterfront

Bed and Breakfast in Chesapeake Bay, NC

Reasons to book

About this bed and breakfast

Amenities

Map of Chesapeake Bay, NC

Nearby attractions

Available Rooms

Deluxe Room, 1 Queen Bed

Deluxe Room, 1 King Bed, Accessible

Luxury Suite, 1 Bedroom, Balcony

Junior Suite, 1 King Bed with Sofa bed

Luxury Cottage, 1 Bedroom, Kitchen, River View

Reviews

FAQs

How much does this bed and breakfast cost compared to others in Chesapeake Bay?

Is parking included with this bed and breakfast?

Is there a pool at this bed and breakfast?

Is The Oaks Waterfront pet friendly?

What amenities are available at The Oaks Waterfront?

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