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Saint Michaels
The Oaks Waterfront Hotel
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The Oaks Waterfront Hotel Saint Michaels Exterior photoThe Oaks Waterfront Hotel Saint Michaels Interior photoThe Oaks Waterfront Hotel Saint Michaels Exterior photo

THE OAKS WATERFRONT HOTEL

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Check rooms and rates
From$939 /night
Check-in
10Jun
Check-out
11Jun
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

25876 Royal Oaks Road, Saint Michaels, MD 21662
-
Near the Chesapeake Bay Maritime Museum
Perfect
9.5
9.8
/10
4.8
4.8
/5

Loved by The Oaks Waterfront Hotel guests

personal boat ride
crab cake
free use bikes
paddle boards kayaks
complimentary breakfast
"The renovations are beautiful and peaceful and the grounds are perfectly manicured with views on the water."
Picky1234 from United States
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"Our room was extremely comfortable, and the chef prepared evening meals were 5 star!"
Kathy H from United States
read full review
"The entire hotel was very beautiful as my wife kept commenting."
Jim R. from United States
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"The Oaks provided us with a fantastic experience for our weekend getaway."
Somecomments from United States
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Waterfront boutique hotel with luxury cottages and complimentary outdoor activities in Saint Michaels

Accommodations

The Oaks Waterfront Hotel offers renovated rooms and suites with high-end furnishings, flat-screen TVs, and private bathrooms stocked with bathrobes and complimentary toiletries. Guests seeking more space can book one of the private cottages, such as Cottage 1 or Acorn Cottage, each featuring a covered porch with waterfront views. All accommodations are air-conditioned and include a full-size refrigerator, while cottage bathrooms have heated floors and a soaking tub.

Dining

The on-site Oak Room restaurant serves dinner several nights a week, with an executive chef who also owns a local bistro in St. Michaels. A complimentary cooked-to-order breakfast is included with every stay, offering options like French toast, omelets, and crab omelets. The bar features craft cocktails and a wine list with selections from affordable to premium bottles.

Activities & Amenities

Guests have complimentary use of bicycles, kayaks, paddleboards, and canoes to explore Oak Creek and the surrounding waterfront. The property features a seasonal outdoor saltwater swimming pool with sun loungers and umbrellas, plus yoga classes. A rooftop terrace and multiple decks with Adirondack chairs overlook the water and manicured gardens.

Services & Pet-Friendly Policies

The hotel provides a complimentary driver service to town and a shuttle for local destinations. Pets are welcome, with pet baskets and bowls provided, and the property has a designated smoking area. Other services include a 24-hour front desk, concierge, luggage storage, and electric vehicle charging stations.

Events & Weddings

The Oaks Waterfront Hotel is a venue for weddings and events, with a spacious outdoor lawn and a beautifully renovated event space. The property can host rehearsal dinners, welcome parties, and receptions, with catering from the on-site Oak Room restaurant. Groups can book multiple cottages and rooms for a full weekend celebration.

Highlights

Location: 10-acre waterfront property near St. Michaels and natural parks

Accommodations: Luxury cottages with water views and renovated suites

Dining: On-site Oak Room with local culinary focus and free cooked-to-order breakfast

Activities: Complimentary kayaks, paddleboards, bicycles, and fishing charters

Services: Complimentary driver service to town, pet-friendly, electric vehicle charging

Ideal for: Couples seeking a wedding venue, travelers wanting a peaceful waterfront retreat

“I was struck by the serene atmosphere here, a genuinely peaceful escape with beautifully maintained grounds that lead right to the water's edge. The attention to detail in the renovations and the comfortable, stylish rooms create a sense of refined comfort, and I found the staff consistently helpful and welcoming. It's a place that manages to feel both elegant and intimately tranquil, leaving one feeling truly refreshed.”
Hotel logo
James DavidEditor-in-Chief at Usmaryland

Select your room type

The Oaks Waterfront Hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
    One-Bedroom Cottage
    2 persons
    37 sq. feet
    1 King-size bed
    Air conditioning
    Bathtub
    room details
    Junior Suite
    2 persons
    1 King-size bed
    Air conditioning
    Heating
    room details
    King Room
    2 persons
    1 King-size bed
    Air conditioning
    Bathtub
    room details
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!
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Check-in/ Check-out

Facilities

The Oaks Waterfront Hotel offers amenities for your comfortable stay and unforgettable experiences
Facilities: Perfect
9.6/10Review score

General

  • No smoking on site
  • Parking
  • Safe deposit box
  • 24-hour reception
  • Express check-in/ -out
  • Pets allowed
  • 24-hour security
  • Luggage storage
  • Lift
  • Fireplace
  • Smoke detectors
  • Electric vehicle charging station
  • Fire extinguishers

Sports & Fitness

  • Canoeing
  • Cycling
  • Golf course
  • Yoga class

Guest Parking

  • Cookware/ Kitchen utensils

Services

  • Free shuttle service
  • Pet amenities available
  • Housekeeping
  • Tours/Ticket assistance
  • Welcome drink

Dining

  • Restaurant
  • Bar/ Lounge area
  • Picnic area/ Tables
  • Packed lunches
  • Special diet menus

Business

  • Meeting/ Banquet facilities

Spa & Leisure

  • Saltwater pool
  • Seasonal outdoor pool
  • Beach umbrellas
  • Sun loungers
  • Sun terrace
  • Garden area
  • Leisure/ TV room

Room features

  • Free Wi-Fi in rooms
  • Air conditioning
  • Heating
  • Sitting area
  • Terrace
  • Garden furniture
  • Tea and coffee facilities
  • Dining table

Bathroom

  • Free toiletries

Self-catering

  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV

Room decor

  • Parquet floor
Show more

The Oaks Waterfront Hotel Location

25876 Royal Oaks Road, Saint Michaels, MD 21662
Explore Saint Michaels
Experience Saint Michaels
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Chesapeake Bay Maritime Museum
Chesapeake Bay Maritime Museum
15-minute drive
Showcases maritime history with interactive exhibits, including a working boatyard and stunning waterfront views.
Saint Marys Square Museum
Saint Marys Square Museum
15-minute drive
Houses artifacts from the local community and offers insights into the culture and history of Saint Michaels.
Plain Dealing
5-minute drive
Historical landmark featuring unique local architecture and displays about the region's rich agricultural past.
Old Woman's Folly
10-minute drive
A natural landmark offering scenic views and local legends, ideal for a quick nature walk or picnic spot.
Chesapeake Bay Fly Fishing
10-minute drive
Thrilling fishing experience in the Chesapeake Bay with guided charters available. Equipment rentals offered.
San Domingo Creek Kayaking
10-minute drive
Relaxing kayaking tours through serene waters, perfect for nature lovers. Rentals and guided tours available.
t at the General Store
5-minute walk
Casual dining with fresh local ingredients. Signature dishes include crab cakes and home-baked desserts.
The Crab Claw
10-minute drive
Classic seafood dining experience with waterfront views. Known for its steamed crabs and local craft beers.
St. Michaels Winery
10-minute drive
Wine tastings and tours in a cozy, inviting atmosphere with locally produced wines and regular live music events.
The Avalon Theatre
15-minute drive
Historic theatre featuring live performances and film screenings. Family-friendly events and local talent shine here.
Getting around
  • City Centre
    Saint Michaels 10 min  ·  3.9 mi
  • Airports
    Salisbury-Ocean City Wicomico Regional (SBY) 150 min  ·  62.1 mi
    Martin State (MTN) 314 min  ·  129.8 mi
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Property information and rules
Check-in
from 15:00-17:00
Check-out
until 11 am
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the hotel rooms for free.
Breakfast
The hotel The Oaks Waterfront provides visitors with a free full breakfast.
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are allowed on request.
Number of rooms:
16

Reviews and Ratings

Feedback about The Oaks Waterfront Hotel from previous guests about their experience.
Review score
Based on 120 verified reviews
9.9 /10
Perfect
99 %
Recommend
Cleanliness
9.2/10
Comfort
10.0/10
Facilities
9.6/10
Free WiFi
10.0/10
Location
9.6/10
Staff
9.6/10
Value for money
9.5/10
Guest reviews
based on 23 reviews
9.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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Check-in
10Jun
Check-out
11Jun
Rooms and Guests2 Guests, 1 Room
  • Overview
  • Rooms
  • Price calendar
  • Facilities
  • Location
  • Reviews