No shortcuts have been made at our fully renovated St. Michaels hotel and waterfront event venue in Maryland. At The Oaks, we have used the finest amenities, modern aesthetics and high-end furnishings to create a first-class experience for our guests. Our goal is to exceed your expectations during your next Eastern Shore getaway.
Deluxe Rooms
| Room | Guests | Bed | Bath | Features | ||
|---|---|---|---|---|---|---|
 | Room 20 | Two | Queen | Walk-in Shower | 2nd Floor | Check Rates |
 | Room 21 | Two | King | Tub/Shower Combo | 2nd Floor | Check Rates |
 | Room 22 | Two | Queen | Walk-in Shower | 2nd Floor, Waterview | Check Rates |
 | Room 23 | Two | King | Walk-in Shower | 2nd Floor, Partial Waterview | Check Rates |
 | Room 25 – ADA | Two | King | Roll-in Shower With Bench | 2nd Floor, ADA Accessible, Partial Waterview | Check Rates |
 | Room 28 | Two | 2 Queens | Walk-in Shower | 2nd Floor | Check Rates |
 | Room 30 | Two | Queen | Walk-in Shower | 3rd Floor | Check Rates |
 | Room 32 | Two | King | Walk-in Shower | 3rd Floor, Partial Waterview | Check Rates |
Suites
| Room | Guests | Bed | Bath | Features | ||
|---|---|---|---|---|---|---|
 | Junior Suite – Room 29 | Four | King | Walk-in Shower | 2nd Floor, Pull-out Sofa, Waterview | Check Rates |
 | Junior Suite – Room 33 | Two | King | Walk-in Shower | 3rd Floor, Private Deck, Waterview | Check Rates |
 | One Bedroom – Waterfront Suite | Four | King | Soaking Tub & Shower | 2nd Floor, Two-Room Suite, Two Private Decks, Pull-out Sofa, Wet Bar, Waterview | Check Rates |
Private Cottages
| Room | Guests | Bed | Bath | Features | ||
|---|---|---|---|---|---|---|
 | Cottage 1 | Two | King | Soaking Tub & Shower | 1st Floor, Outdoor Waterfront Seating, Full Kitchen, Fireplace, Pet Friendly | Check Rates |
 | Cottage 2 | Two | King | Soaking Tub & Shower | 1st Floor, Outdoor Waterfront Seating, Pet Friendly | Check Rates |
 | Cottage 3 | Two | King | Soaking Tub & Shower | 1st Floor, Outdoor Waterfront Seating, Pet Friendly | Check Rates |
 | Cottage 4 | Two | King | Soaking Tub & Shower | 1st Floor, Outdoor Waterfront Seating, Pet Friendly | Check Rates |
In-Room Amenities
- Complimentary Wi-Fi
- TVs Equipped with Apple TV
- Robes
- Clothing Steamer
- Heated Bathroom Floors
- Hairdryers
- Individual Climate Control
- Wet Bar in Waterfront Suite
- Full Kitchen in Cottage 1
Property Amenities
- Complimentary Breakfast Served Daily
- Complimentary Wi-Fi
- Saltwater Pool
- Complimentary Bicycles with Helmets
- Complimentary Kayaks & Paddleboards
- Waterside Seating
- Fire Pits
- Complimentary Driver to Town
- Complimentary On-site Parking
- Electric Vehicle Chargers
- On-site Staff Available 24/7
- Daily Housekeeping Included
The Oak Room Restaurant
The Oak Room is our on-site restaurant, where in-house guests can enjoy breakfast and dinner daily:
**Breakfast for In-House Guests**
Monday – Saturday: 8:00 AM – 10:00 AM
Sunday: 8:00 AM – 10:00 AM
**Dinner for In-House Guests**
Monday – Sunday: 4:00 PM – 8:00 PM
The Oak Room welcomes the public to dine with us on certain days. Please click here to view our current public dining calendar.
Tariffs
Main House guest rooms range from $389 to $800 a night (a full breakfast is included in the room rate). Please call 410-745-5053 for more details. Visa, Mastercard, American Express, Discover, Cash or Check are accepted. A 6% Maryland sales tax and 4% Talbot County Room Tax are applied to all room tariffs.
Reservations
Call us for the guaranteed lowest rate at 410-745-5053. Reservations are guaranteed with a major credit card.
Check In & Check Out
Open 24 Hours
Check In: 3:00 pm to 5:00 pm. If you are planning to arrive after 5:00 p.m., please call the front desk to make late arrival arrangements.
Check Out: Please check out by 11:00 am.
Cancellations
A credit card is required to guarantee your reservation. If booking through a third party, please make note of their cancellation policy.
Cancellation Policy: If your plans change after your reservation is confirmed, cancellation notice is required 14 days in advance of your arrival date. You will be refunded your deposit, minus a $50 Cancellation Fee.
If you cancel your reservation 14 days or less prior to arrival date, your deposit will be forfeited in addition to a $50 Cancellation Fee. Your credit card on file will be charged.
The Cancellation Fee also applies to changes in your arrival/departure date which result in a shorter stay. No refunds are provided for late arrivals or early departures.
Breakfast
A hot breakfast is served daily from 8:30 am – 9:30 am in the Breakfast Room. Please let us know of food allergies and intolerances.
Pets
Our private cottages are available as dog-friendly. Canines are welcome with a non-refundable $150 dog fee per guestroom, per stay, per dog. Please notify us when making a reservation, and dogs must be registered at check-in. For our complete pet policy, please refer to The Oaks Waterfront Hotel Dog Occupancy Agreement (PDF), which must be acknowledged and submitted to the hotel at check-in.
Additional Policies
- The Oaks is a smoke free facility. Smoking is permitted outside, only.
- Rooms are based on double occupancy. We can arrange for breakfast for any additional guests. Charges for additional guests vary based on age.
