Compare Woolford Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Woolford Cottages

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Pet friendly
Waterfront property with private boat ramp and new dock!

Waterfront property with private boat ramp and new dock!

At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Cozy Cottage with access to and partially obstructed views of the bay.

Cozy Cottage with access to and partially obstructed views of the bay.

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Woolford
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Woolford

    Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

    Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

    Woolford
    9.8/10 Exceptional! (58 reviews)
    Hyatt Regency Chesapeake Bay

    Hyatt Regency Chesapeake Bay

    100 Heron Blvd, Cambridge, MD
    $233 nightly
    The price is $265 total per night from Oct 12 to Oct 13
    $265 total
    Oct 12 - Oct 13
    Total with taxes and fees
    8.6/10 Excellent! (1,003 reviews)
    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street, St. Michaels, MD
    $95 nightly
    The price is $105 total per night from Oct 13 to Oct 14
    $105 total
    Oct 13 - Oct 14
    Total with taxes and fees
    8/10 Very Good! (1,000 reviews)

Cottages

Book a cottage in Woolford
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Woolford. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Woolford better.

Cottage apartments in Woolford range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Woolford
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Woolford and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Woolford cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Woolford. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Woolford Cottages essential information

Accommodation
62 Cottages
Lowest Price
$105
Highest Price
$265
Popular accommodation
Family and Pet-Friendly, Waterfront with Pier, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly), Waterfront Cottage in Beautiful Hoopers Island, Waterfront property with private boat ramp and new dock! , The Middle Point Cabin in Saint Michaels, Cozy Cottage with access to and partially obstructed views of the bay.

Explore More Ways to Travel with Travelocity