Deals on vacations and trips to Woolford

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Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $795, price is now $754 per person
$754
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
The Shore House

The Shore House

2 out of 5
West Ocean City
Price was $2,307, price is now $1,982 per person
$1,982
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A seasonal outdoor pool and laundry facilities are also provided.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,293, price is now $2,134 per person
$2,134
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
Price was $900, price is now $852 per person
$852
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and express check-out are also offered.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,138, price is now $1,084 per person
$1,084
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

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
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

Woolford MD
Get rates
This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. There's a sauna on site, and laundry facilities and concierge services are also offered.
Pool
Hot Tub
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
$184 nightly
The price is $209 total per night
$209 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.
On private beach
Pool
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$517 nightly
The price is $568 total per night
$568 total
Dec 14 - Dec 15
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy the 3 outdoor tennis courts and perks like free valet parking and free WiFi.
Pool
Hot Tub
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $197 total per night
$197 total
Dec 14 - Dec 15
Total with taxes and fees
This traditional hotel features a full-service spa and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Spa
Parking included
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free Cancellation
$105 nightly
The price is $116 total per night
$116 total
Dec 18 - Dec 19
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.
Pool
Breakfast included
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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 $754, 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 55 mi 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 50 mi northwest of the city center. Other options available to you are Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (55 mi away from central Woolford) and Salisbury - Ocean City Wicomico Regional Airport (SBY) (40 mi 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

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