Book Exclusive Woolford Vacation Packages

Choose one or more items to build your trip:

Top Woolford hotels deals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Get rates
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad National Historical Park are located nearby.
Kitchen
Washer
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

Woolford MD
Get rates
Book a stay at this beach vacation home in Woolford. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Ragged Island and Spocott Windmill are located nearby.
Pool
Hot tub
"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
Get rates
Stay at this vacation home in Woolford. Enjoy private pools, laundry facilities, and patios. Popular attractions Ragged Island and Spocott Windmill are located nearby.
Pool
Kitchen
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Free cancellation
Reserve now, pay when you stay
The price is CA $252 per night
CA $252
CA $351 total
Mar 23 - Mar 24
includes taxes & fees
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.
On private beach
Pool
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free cancellation
Reserve now, pay when you stay
The price is CA $126 per night
CA $126
CA $139 total
Mar 18 - Mar 19
includes taxes & fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saint Michaels Village and Classic Motor Museum are located nearby.
Pool
Breakfast included
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
The price is CA $503 per night
CA $503
CA $553 total
Mar 24 - Mar 25
includes taxes & fees
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Chesapeake Bay Maritime Museum and 1879 Hooper Straight Lighthouse are located nearby.
Pool
Hot tub
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.

Popular places to visit

Woods Island

Commune with nature and explore the great outdoors at Woods Island during your travels in Woolford.

Woods Island

Frequently asked questions

How much are vacation packages to Woolford?
With vacation packages on offer from as little as , there's no need to empty your piggy bank to visit Woolford. Travelocity can help. Bundle your experiences, flights and hotels into a convenient package and score impressive discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Woolford?
Book your dream vacation with Travelocity. With access to 400 airline partners and at least 1,000,000 hotels all over the world, selecting the perfect Woolford package deal couldn't be simpler.
Why should I purchase my Woolford vacation package with Travelocity?
Whether you're searching for the ultimate unplugged escape or you crave the fun and excitement of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to comb through countless websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our professional customer service experts are available round-the-clock.
Will I save money on my Woolford car rental if I combine it with a hotel or flight?
With a Woolford vacation package, you can bundle your hotel, flight and car bookings and save loads. If you're eager to see the best of this exciting city, why not make a beeline for White House? This famous sight is 88 kilometers from Woolford. With your own rental car, you'll be there belong long.
Which airport is best for Woolford?
Ronald Reagan Washington National Airport (DCA) is one of the biggest airports in Woolford. It's roughly 80 kilometers northwest of the city center. Other options available to you are Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (88 kilometers away from central Woolford) and Salisbury - Ocean City Wicomico Regional Airport (SBY) (64 kilometers away from central Woolford).
Where should I stay when visiting Woolford?
The The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks is the number one choice of many visitors. Book as soon as possible before it's too late.

Photos of local treasures

Browse Woolford vacation photos for more inspiration

Birds - Cattle Egret, Blackwater National Wildlife Refuge, Virginia
Birds - Cattle Egret, Blackwater National Wildlife Refuge, Virginia