Save
up to 10%
when booking directly with us!
Check rooms and rates
From459US$ /night
Check-in
31Dec2025Select date
Check-out
01Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

25876 Royal Oaks Road, Saint Michaels, Maryland, United States, MD 21662
-
Near San Domingo Creek
Perfect
9.7
9.8
/10
4.8
/5

The Oaks Waterfront Hotel - A Rural Waterfront Retreat with Seasonal Pool, Rooftop Terrace and Free Cooked Breakfast

Situated along a secluded cove, this 4-star Saint Michaels hotel features 15 air-conditioned rooms with private bathrooms, heated floors, and modern amenities. The Oaks Waterfront provides complimentary cooked-to-order breakfast, Wi-Fi, and self-parking. Room options include suites with soaking tubs and cottages with full kitchens and waterfront views. The seasonal saltwater pool operates from May, while guests can enjoy complimentary bicycles, kayaks, and paddleboards. A 24-hour front desk, concierge services, and business center cater to various needs. The property includes a rooftop terrace, garden, and shared lounge. Located 62 miles from Salisbury-Ocean City Wicomico Regional Airport, The Oaks offers proximity to landmarks like The Third Haven Friends Meeting House.

Pros

Professional host management ensures consistent service standards

Complimentary driver service to town available

Electric vehicle charging stations on premises

Daily housekeeping included with stay

Fire pits and waterside seating areas throughout the property

Cons

Pool access limited to seasonal operation

No pets or service animals permitted

“For a quiet waterfront wedding, or simply a peaceful escape, this address just outside St. Michaels distinguishes itself with renovated rooms and discreet service. I was particularly impressed by the thoughtful extras: kayaks, bikes, and even fishing gear are all available for guest use. Its unique cottages promise both privacy and exceptional water views.”
Hotel logo
Isabella MooreSenior Editorial Director at Petfriendlyhotels
View all

Select your room type

Cozy rooms, spacious suites, and family-friendly homes, all with flexible cancellation policies & special deals
One-Bedroom Cottage
2 persons
37 m² 
1 King-size bed
Shower
Coffee machine
Junior Suite
2 persons
1 King-size bed
Shower
Heating
King Room
2 persons
1 King-size bed
Shower
Heating
Deluxe Double Room
2 persons
2 King Size Beds
Shower
Heating
Click button to see more rooms
Show all rooms
Show all roomsLess

Price and room availability calendar

Check availability and rates for your selected dates!

Facilities

Enjoy premium amenities for a relaxing stay with your pet

General

  • No smoking on site
  • Free Wi-Fi
  • 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

Location

25876 Royal Oaks Road, Saint Michaels, Maryland, United States, MD 21662
Map view
25876 Royal Oaks Road, Saint Michaels, Maryland, United States, MD 21662
Nearby
Royal Oak Community United Methodist Church
590 m
Restaurants
t at the General Store
380 m
25942 Royal Oak Rd
Explore Saint Michaels
Explore the Area
Top Attractions
Activities
Dining
Entertainment
Chesapeake Bay Maritime Museum
Chesapeake Bay Maritime Museum
15 minutes' drive
A premier maritime museum featuring historic boats and exhibits dedicated to the Chesapeake Bay's history and ecology.
Saint Paul Church
25 minutes' walk
A historic church known for its stunning architecture and serene atmosphere, often hosting community events.
Graul's Market St. Michaels
Graul's Market St. Michaels
10 minutes' drive
A charming market offering local produce, gourmet foods, and handmade goods, perfect for a unique shopping experience.
1879 Hooper Strait Lighthouse
1879 Hooper Strait Lighthouse
15 minutes' drive
An iconic lighthouse housing maritime artifacts and offers guided tours, showcasing the rich nautical history of the area.
Water Sports at St. Michaels
10 minutes' drive
Enjoy kayaking, paddleboarding, and boating on the scenic Miles River. Rentals available at local shops.
Yoga by the Bay
15 minutes' drive
Relax with guided yoga sessions on the waterfront, perfect for all skill levels. Classes are offered seasonally.
t at the General Store
t at the General Store
5 minutes' walk
A cozy eatery known for its farm-to-table dishes, warm atmosphere, and local wine selection. Reservations recommended.
The Crab Claw
15 minutes' drive
Renowned for its steamed crabs and casual waterfront dining, offering fresh seafood and picturesque views.
The St. Michaels Playhouse
10 minutes' drive
A community theater featuring various performances, including musicals and plays. Family-friendly shows available.
Lucky's
15 minutes' drive
A lively bar offering live music and karaoke nights, creating a vibrant atmosphere for a fun night out.
Getting around
City Centre
Saint Michaels10 min  ·  6.2 km
Airports
Salisbury-Ocean City Wicomico Regional Airport (SBY)150 min  ·  99.9 km
Baltimore, MD (MTN)314 min  ·  208.8 km
Looking for exclusive early booking discounts?
Unlock special rates for your next adventure with your pet today!
Check Rates
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
is available in 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
FAQs
About The Oaks Waterfront Hotel
What is the check-in and check-out policy at The Oaks Waterfront Hotel?
Check-in is at 15:00, and check-out is by 11:00.
What nearby attractions can be found close to The Oaks Waterfront Hotel?
Nearby attractions include The Third Haven Friends Meeting House (5 km), Oxford Museum (6 km), and Annapolis (38 km).
Is there parking available at The Oaks Waterfront Hotel?
Complimentary private parking is available on-site without reservation required.
Does The Oaks Waterfront Hotel provide Wi-Fi for guests?
Complimentary Wi-Fi is available throughout the property.
What room amenities can guests expect at The Oaks Waterfront Hotel?
Rooms feature air conditioning, a flat-screen TV with cable, private bathrooms, bathrobes, and complimentary toiletries.
Are there any dining options available at The Oaks Waterfront Hotel?
The hotel offers an on-site restaurant and a seasonal outdoor saltwater pool where guests can enjoy their meals.
What recreational activities are available at The Oaks Waterfront Hotel?
Guests can enjoy complimentary use of bicycles, canoeing, and access to a seasonal outdoor swimming pool.
How far is The Oaks Waterfront Hotel from Baltimore - Washington International Airport?
The hotel is located 64 km from Baltimore - Washington International Airport.
Does The Oaks Waterfront Hotel offer any safety features?
Safety features include fire extinguishers, smoke detectors, and a first aid kit.
What outdoor amenities does The Oaks Waterfront Hotel provide?
The hotel has a rooftop terrace, a garden with picnic area/tables, and sun loungers for guest relaxation.
Are there any business services available at The Oaks Waterfront Hotel?
The hotel includes a business center to assist guests with professional needs.

Next best alternative

Consider them for your next trip.
Check-in
31Dec2025Select date
Check-out
01Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Need more options?
Check Top hotels near The Oaks Waterfront Hotel
St. Michaels Inn Exterior photo
Mobile-only price

St. Michaels Inn

7.6
Very good958 reviews
3653m from property
USD 109USD 98
per night
St Michaels Harbour Inn, Marina And Spa Saint Michaels Exterior photo
Mobile-only price

St Michaels Harbour Inn, Marina And Spa Saint Michaels

8.8
Great443 reviews
5721m from property
USD 135USD 121
per night
The Wildset Hotel Saint Michaels Exterior photo
Mobile-only price

The Wildset Hotel Saint Michaels

9.0
Perfect128 reviews
6234m from property
USD 640USD 576
per night