The Oaks Waterfront Hotel Saint Michaels Interior photo

The Oaks Waterfront Hotel Saint Michaels Room photo

The Oaks Waterfront Hotel Saint Michaels Exterior photo

Key details

About the Hotel

25876 Royal Oaks Road, Saint Michaels, MD 21662

Near the Chesapeake Bay Maritime Museum

Perfect

9.3

9.8

/10

4.9

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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Boutique hotel on the Miles River offering free breakfast, bicycles, kayaks, and paddleboards

Rooms and Cottages

Renovated accommodations include Junior Suites and Deluxe Kings with private bathrooms and flat-screen televisions. The property also offers separate luxury cottages, such as the Acorn Cottage, with water views and private porches. A rooftop terrace provides panoramic views of Oak Creek and the Miles River.

Dining

Free cooked-to-order breakfasts are served each morning; choices include omelets, French toast, and biscuits with sausage gravy. The Oak Room restaurant offers dinner several nights a week with a full bar and wine list. Happy hour specials include local oysters, and the restaurant can accommodate special diet menus.

Activities

Guests can use complimentary bicycles, kayaks, and paddleboards to explore the waterfront and nearby parks. A seasonal saltwater swimming pool is open during warmer months, with sun loungers and umbrellas. The area is popular for canoeing, and a golf course is accessible nearby.

Services and Transportation

A hotel shuttle and complimentary driver service provide transportation to Saint Michaels and surrounding towns. Free parking and an electric vehicle charging station are available on-site. The 24-hour front desk offers concierge services, luggage storage, and express check-in/check-out.

Events and Meetings

The Oaks has a waterfront event space that accommodates weddings, receptions, and business meetings. The grounds include extensive outdoor areas, a garden, and a covered dock for events. Meeting and banquet facilities are available, and a tour desk can assist with group activities.

Highlights

Location: Waterfront on the Miles River, 38 km from Annapolis

Rooms: Renovated suites and luxury cottages with water views

Dining: Free cooked-to-order breakfast and Oak Room dinner menu

Activities: Complimentary bicycles, kayaks, paddleboards; saltwater pool

Services: Complimentary driver service, shuttle, free parking, EV charging

Pet-Friendly: Pet bowls and baskets provided; smoke-free property

“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
400 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!

Facilities

The Oaks Waterfront Hotel offers amenities for your comfortable stay and unforgettable experiences

Facilities: Perfect

9.1/10Review score

General

No smoking on site
Parking
Safe deposit box
24-hour reception
Express check-in/ -out
No 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

Private parking is possible on site for free.

Services

Free shuttle service
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

The Oaks Waterfront Hotel Location

25876 Royal Oaks Road, Saint Michaels, MD 21662

Map view

City landmarks

Landmark

Saint Paul Church

4900 ft

Landmark

Plain Dealing

1.3 mi

Museum

Chesapeake Bay Maritime Museum

3.7 mi

Landmark

Old Woman's Folly

1.8 mi

Landmark

Perry Hall

2.1 mi

Market

Graul's Market St. Michaels

2.4 mi

Landmark

Chesapeake Bay Fly Fishing

2.6 mi

Landmark

San Domingo Creek

3.0 mi

Landmark

Guyette and Schmidt Retail Gallery

3.0 mi

Landmark

Ferry Neck Church

3.1 mi

Gallery

Ouvert Gallery

3.7 mi

Museum

Saint Marys Square Museum

3.6 mi

Landmark

Custom House

3.6 mi

Gallery

Hopkins Original Art

3.6 mi

Lighthouse

1879 Hooper Strait Lighthouse

3.9 mi

Landmark

Simply Dragonfly

3.8 mi

Museum

Oxford Museum

3.8 mi

Nearby

Royal Oak Community United Methodist Church

2000 ft

Restaurants

t at the General Store

1300 ft

25942 Royal Oak Rd

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.

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.

Cleanliness

9.1/10

Comfort

10.0/10

Facilities

9.1/10

Free Wi-Fi

10.0/10

Location

9.4/10

Staff

9.5/10

Value for money

9.4/10

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THE OAKS WATERFRONT HOTEL

About the Hotel

Loved by The Oaks Waterfront Hotel guests

Rooms and Cottages

Dining

Activities

Services and Transportation

Events and Meetings

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

The Oaks Waterfront Hotel Location

Reviews and Ratings

Next best alternative

Popular hotels all over the world