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The Oaks Waterfront

Property class: 4

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Photo gallery for The Oaks Waterfront

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools. - The Oaks Waterfront (Easton)
A wooden console table with framed floral artwork, two lamps, and two ottomans. - The Oaks Waterfront (Easton)
A white colonial-style house with a covered porch, brick steps, and outdoor seating. - The Oaks Waterfront (Easton)
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs. - The Oaks Waterfront (Easton)
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock. - The Oaks Waterfront (Easton)
Take advantage of free cooked-to-order breakfast, a rooftop terrace, and a garden at The Oaks Waterfront. Treat yourself to a massage or other spa services. Stay connected with free in-room WiFi, and guests can find other amenities such as a bar and a business center.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Spa
  • Parking included
  • Free WiFi

Off-peak, on budget: 30% or more off select hotels in our fall sale

Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

Room options

Available filters for rooms
Showing 15 of 15 rooms

View all photos for Deluxe Room, 1 Queen Bed

A bedroom with a large bed, a blue armchair, a nightstand with a lamp, and a window with curtains.

Deluxe Room, 1 Queen Bed

  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Deluxe Room, 1 King Bed, Accessible

A neatly arranged bedroom with a large bed, bedside tables, a chair, and a small table with a lamp.

Deluxe Room, 1 King Bed, Accessible

10.0 out of 10
Exceptional
(2 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Luxury Suite, 1 Bedroom, Balcony

A bedroom with a large bed, two bedside tables, a chair, and a window with a view.

Luxury Suite, 1 Bedroom, Balcony

  • Water view
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

View all photos for Junior Suite, 1 King Bed with Sofa bed

A bedroom with a large bed, a sofa, a side table, and a lamp.

Junior Suite, 1 King Bed with Sofa bed

10.0 out of 10
Exceptional
(1 review)
  • Water view
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

View all photos for Luxury Cottage, 1 Bedroom, Kitchen, River View

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

Luxury Cottage, 1 Bedroom, Kitchen, River View

  • Water view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Junior Suite, 1 King Bed, Balcony

A hotel room with a large bed, two armchairs, a small table with a lamp, and two framed botanical prints on the wall.

Junior Suite, 1 King Bed, Balcony

10.0 out of 10
Exceptional
(2 reviews)
  • Water view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Deluxe Room, 1 Queen Bed

A hotel room with a large bed, a sitting area with a chair, a small table, and a mirror.

Deluxe Room, 1 Queen Bed

10.0 out of 10
Exceptional
(2 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Deluxe Room, 1 King Bed

A neatly arranged bedroom with a large bed, bedside tables, a chair, and a desk.

Deluxe Room, 1 King Bed

10.0 out of 10
Exceptional
(5 reviews)
  • Water view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Deluxe Room, 1 Queen Bed

A hotel room with a large bed, two armchairs, a small table with a lamp, and two framed botanical prints on the wall.

Deluxe Room, 1 Queen Bed

  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Deluxe Room, 1 King Bed, Private Bathroom

A neatly arranged bedroom with a large bed, bedside tables, a chair, and framed artwork on the walls.

Deluxe Room, 1 King Bed, Private Bathroom

  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Luxury Cottage, 1 King Bed, River View

A living room with a sofa, armchairs, a coffee table, and artwork on the wall.

Luxury Cottage, 1 King Bed, River View

  • Water view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Deluxe Room, 1 Queen Bed

A bedroom with a bed, a desk, a chair, and a window.

Deluxe Room, 1 Queen Bed

  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Luxury Cottage, 1 King Bed, River View

A white colonial-style house with a covered porch, brick steps, and outdoor seating.

Luxury Cottage, 1 King Bed, River View

  • Water view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Deluxe Room, 2 Queen Beds

A hotel room with two beds, a chair, a small table, and a lamp.

Deluxe Room, 2 Queen Beds

10.0 out of 10
Exceptional
(3 reviews)
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Luxury Cottage, 1 King Bed, River View

A bedroom with a large bed, bedside tables, a bench, and a window with curtains.

Luxury Cottage, 1 King Bed, River View

  • River view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

About the neighborhood

Located in Easton, The Oaks Waterfront is in a rural area and on the waterfront. St. Michaels Winery and Windon Distilling are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chesapeake Bay Maritime Museum and Phillips Wharf Environmental Center. Take an opportunity to explore the area for outdoor excitement like hiking/biking trails. Visit our Easton travel guide
View more B&B in Easton
Map
25876 Royal Oak Road, Royal Oak, Easton, MD, 21662

What's nearby

  • A white wooden house with a brown door and a small window.
    Saint Michaels Village
    5 min drive - 3.7 miles
  • A marina with several sailboats docked in calm waters.
    St. Michaels Marina
    7 min drive - 4.9 miles
  • A lighthouse on stilts with a green roof, surrounded by water and greenery.
    Chesapeake Bay Maritime Museum
    8 min drive - 5.4 miles
  • St. Michaels Winery
    6 min drive - 4.5 miles
  • St. Michaels Museum
    6 min drive - 4.7 miles

Getting around

  • Cambridge Station
    36 min drive
  • Easton, MD (ESN-Easton - Newnam)
    16 min drive

Restaurants

  • Foxy's Harbor Grille
    7 min drive
  • The Crab Claw
    8 min drive
  • Doc's Sunset Grille
    27 min drive
  • Ava's Pizzeria & Wine Bar - St Michaels
    7 min drive
  • Talbot St. Tavern
    7 min drive

Similar properties

Front of property
St Michaels Inn
St. Michaels
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
8.0 out of 10, Very Good, 1,009 reviews
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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free self parking on site
  • Wheelchair-accessible parking available

Food and drink

  • Free cooked-to-order breakfast available daily
  • A bar/lounge
  • A restaurant
  • Coffee and tea in common areas

Things to do

  • Bicycle rentals
  • Kayaking
  • Paddleboard
  • Seasonal outdoor pool

Family friendly

  • Seasonal outdoor pool

Conveniences

  • 24-hour front desk
  • Luggage storage

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Proposal/romance packages
  • Tour and ticket assistance

Business services

  • Business center
  • Meeting rooms

Outdoors

  • Garden
  • On the waterfront
  • Picnic area
  • Rooftop terrace

Spa

  • Massage
  • Spa services

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Elevator
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible business center
  • Wheelchair-accessible lounge
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible path to elevator
  • Wheelchair-accessible registration desk

More

  • 2 buildings
  • 3 floors
  • Ballroom
  • Smoking not allowed

Room amenities

Bedroom

  • Premium bedding

Bathroom

  • Bathrobes
  • Free toiletries
  • Hair dryer
  • Heated bathroom floor
  • Private bathroom
  • Toothbrush and toothpaste (on request)
  • Towels provided

Entertainment

  • Smart TV with digital channels

Food and drink

  • Free bottled water

More

  • Air conditioning (climate-controlled)
  • Iron/ironing board

Policies

Check-in

Check-in start time: 3 PM; Check-in end time: 5 PM
Early check-in subject to availability
Late check-in subject to availability
Minimum check-in age: 18

Check-out

Check-out before 11 AM
Late check-out subject to availability

Special check-in instructions

Guests must contact the property in advance for check-in instructions; front desk staff will greet guests on arrival at the property
To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation
If you are planning to arrive after 5 PM please contact the property in advance using the information on the booking confirmation
For any questions, please contact the property using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools
Check-in is from 3-5 PM.

Access methods

Staffed front desk

Pets

Pets not allowed (service animals are welcome, and are exempt from fees)

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Safety features at this property include a fire extinguisher, a smoke detector, and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property

We should mention

The seasonal pool will be open from May to September
Reservations are required for massage services; reservations can be made by contacting the property prior to arrival, using the contact information on the booking confirmation

Frequently asked questions

Does The Oaks Waterfront have a pool?

Yes, this property has a seasonal outdoor pool.

Is The Oaks Waterfront pet-friendly?

No, only service animals are welcome at the property.

How much is parking?

Self parking is free at this property.

What time is check-in at The Oaks Waterfront?

Check-in start time: 3 PM; Check-in end time: 5 PM. Late check-in is available during limited hours.

What time is check-out at The Oaks Waterfront?

Check-out is at 11 AM.

Where is The Oaks Waterfront located?

Situated on the waterfront, this bed & breakfast is 2.9 mi (4.6 km) from Saint Michaels Village and within 6 mi (10 km) of St. Michaels Winery and Windon Distilling. Classic Motor Museum and St. Michaels Museum are also within 6 mi (10 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

The Oaks Waterfront Reviews

10

Exceptional

10

Cleanliness

9.8

Amenities

10

Staff & service

10

Property conditions & facilities
Rating 10 - Excellent. 42 out of 44 reviews
Rating 8 - Good. 2 out of 44 reviews
Rating 6 - Okay. 0 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 0 out of 44 reviews

Reviews

Verified review

10/10 Excellent

Seth

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property, wonderful staff, excellent food service.
Stayed 2 nights in Feb 2025
Verified review

10/10 Excellent

Connie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property, great service, wonderful breakfast.
Stayed 2 nights in Aug 2023
Verified review

10/10 Excellent

Barbara

Liked: Cleanliness, amenities, property conditions & facilities
Loved the Oaks! Fabulous accommodations and excellent staff
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

James

Liked: Cleanliness, amenities, property conditions & facilities
Our stay at The Oaks exceeded our expectations. It was recommended to us by a family friend. All staff were very informative and helpful. We will definitely make it a point to return.
Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

EDMUND

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful facility and grounds and friendly staff.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

diane mc

Liked: Cleanliness, staff & service, property conditions & facilities
delightful and charming! great views and peaceful! We really enjoyed our stay!
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Cary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!
Stayed 1 night in Sep 2024
Verified review

10/10 Excellent

Deborah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Erin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

FRANCES

Liked: Cleanliness, staff & service, property conditions & facilities
Wonderful place. Beautiful. Staff was top notch. Accommodations were outstanding.
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Get away

Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Richard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Outstanding boutique hotel on the water. Everything is new. Staff is fantastic. Lovely romantic weekend there
Stayed 2 nights in Feb 2024
Verified review

10/10 Excellent

Debra

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!!
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

Kate

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exquisite and gracious service. Stunning appointments throughout. Just beautiful.
Stayed 2 nights in Mar 2024
Verified review

10/10 Excellent

Lili

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

I definitely coming back!

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.
Stayed 2 nights in Aug 2023
Verified review

10/10 Excellent

James

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

Bryan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Howard

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Anniversary extravaganza

Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Geeti

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 2 nights in Apr 2024
Verified review

10/10 Excellent

Sarah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Jeffrey

Liked: Cleanliness, amenities, property conditions & facilities
Staff, breakfast, and room were all superb!
Stayed 3 nights in Aug 2025
Verified review

8/10 Good

Thomas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The facility designed was out standing and the staff was very good.
Stayed 1 night in Aug 2025
Verified review

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Oaks Waterfront was exactly the kind of getaway we were looking for. Tucked away in a quiet, secluded setting, it feels like you’re escaping from everything, yet St. Michaels is only a short ride away thanks to their beautiful shuttle. It really gives you the best of both worlds. What stood out most to us was the family-owned and operated feel. Everyone was genuinely friendly, and there was a warmth about the property that made it feel less like a hotel and more like staying with incredibly hospitable friends. It has a relaxed, welcoming atmosphere that makes it easy to settle in. We stayed in one of the cottages, and it was beautifully appointed with comfortable bedding and thoughtful touches that made it feel luxurious without trying too hard. The entire property is impeccably maintained, and you can tell the owners take great pride in every detail. We also traveled with our two dogs, and they were just as welcome as we were. They loved the cottage, and we appreciated the dog beds, bowls, and bottled water waiting for them. Those little touches made all the difference. The food was fresh and delicious, and the complimentary breakfast each morning was another example of the attention to detail they put into the guest experience. A special thank you to Kathie, Brad, Linda, and the entire team, including housekeeping. Their kindness and genuine hospitality are what make The Oaks such a special place.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

John

Liked: Cleanliness, staff & service, property conditions & facilities
The property is very well maintained, staff is super friendly and property is newly renovated
Stayed 2 nights in Jul 2023