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 | Check Rates |
![]() | Cottage 2 | Two | King | Soaking Tub & Shower | 1st Floor, Outdoor Waterfront Seating | Check Rates |
![]() | Cottage 3 | Two | King | Soaking Tub & Shower | 1st Floor, Outdoor Waterfront Seating | Check Rates |
![]() | Cottage 4 | Two | King | Soaking Tub & Shower | 1st Floor, Outdoor Waterfront Seating | 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
Tariffs
Main House guest rooms range from $350 to $600 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, you are responsible for the entire cost of your reservation plus a $50 Cancelation Fee. Your credit card on file will be charged in full.
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
Although the staff of The Oaks loves pets, some of our guests do not share the same affection. We are unable to allow pets at The Oaks but are happy to provide you with some great boarding options in the area.
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.
Restaurant Facilities
- A hot breakfast is included daily.
- Hotel bar and in-room enhancements available on-site.
- Bistro St. Michaels is just under 4 miles away, in the heart of St. Michaels, MD.