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The Oaks Waterfront Hotel Saint Michaels Exterior photo

The Oaks Waterfront Hotel Saint Michaels Interior photo

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Key details

About the Hotel

25876 Royal Oaks Road, Saint Michaels, MD 21662

Near the Chesapeake Bay Maritime Museum

Perfect

9.4

9.8

/10

4.8

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

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"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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3-star waterfront hotel in Saint Michaels

Accommodations

The Oaks Waterfront Hotel offers 25 guest rooms with picturesque water views. Many rooms feature private balconies or patios for outdoor relaxation. Various room types including King and Double Queen provide options for solo travelers and families.

Dining

On-site dining is available at The Oaks Restaurant, known for its diverse menu featuring fresh local ingredients. Guests can enjoy a complimentary breakfast with a variety of options each morning. The full-service bar offers a selection of wines, cocktails, and local craft beers.

Location

The hotel sits on the waterfront of the picturesque Chesapeake Bay in Saint Michaels, providing easy access to scenic views and outdoor activities. Guests can explore local bike trails, kayak on the bay, or visit nearby historical sites within a short drive. The Oaks Waterfront Hotel is conveniently located just minutes from the vibrant downtown area.

Meeting Facilities

The Oaks Waterfront Hotel caters to business needs with a dedicated conference room that accommodates small to medium-sized gatherings. Equipped with audio-visual technology, the facility is suitable for meetings, workshops, or family reunions. Extensive planning assistance is available to ensure smooth events.

Outdoor Activities

Guests can take advantage of complimentary bikes to explore the surrounding scenic landscapes or relax in hammocks located throughout the property. The heated outdoor pool is open seasonally, providing a comfortable spot to soak up the sun. Access to nearby fishing and boating activities enhances the waterfront experience.

Highlights

Accommodations: 25 guest rooms with water views

Dining: The Oaks Restaurant with fresh local ingredients

Location: Chesapeake Bay waterfront access

Meeting Facilities: Dedicated conference room with audio-visual technology

Outdoor Activities: Heated outdoor pool and complimentary bikes

“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.”

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

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July 2026 - July 2027

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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

Location

25876 Royal Oaks Road, Saint Michaels, MD 21662

Explore Saint Michaels

Experience Saint Michaels

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

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 not allowed.

Number of rooms:

Reviews and Ratings

Feedback about The Oaks Waterfront Hotel from previous guests about their experience.

Review score

Based on 118 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

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THE OAKS WATERFRONT HOTEL

About the Hotel

Loved by The Oaks Waterfront Hotel guests

Accommodations

Dining

Location

Meeting Facilities

Outdoor Activities

Highlights

Select your room type

Price and Room Availability Calendar

Facilities

General

Sports & Fitness

Guest Parking

Services

Dining

Business

Spa & Leisure

Room features

Bathroom

Self-catering

Media

Room decor

Location

Reviews and Ratings

Next best alternative

Popular hotels all over the world