Deals on vacations and trips to Woolford

Save when you book Woolford package deals

Choose two or more items and save on your trip:

Woolford flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 21
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Free self parking, laundry facilities, and free newspapers are also on offer.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 21
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This motel features 20 beach bars and express check-out. Take advantage of the free self parking.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
This hotel features a restaurant and 2 bars/lounges. Enjoy the indoor pool and perks like free WiFi. Self parking and a safe deposit box are also offered on site.
Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
A marina and an indoor pool are featured at this smoke-free apartment. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a picnic area and a virtual front desk.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.

Top Woolford hotels deals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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
$281 nightly
The price is $319 total per night
$319 total
Jun 22 - Jun 23
Total includes 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
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
$81 nightly
The price is $89 total per night
$89 total
Jul 1 - Jul 2
Total includes 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
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $174 total per night
$174 total
Jun 4 - Jun 5
Total includes taxes and fees
This hotel features an outdoor pool, an outdoor tennis court, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
$648 nightly
The price is $713 total per night
$713 total
Jun 8 - Jun 9
Total includes 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
Quality Inn

Quality Inn

2.5 out of 5
8523 Ocean Gtwy, Easton, MD
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $102 total per night
$102 total
Jun 9 - Jun 10
Total includes taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
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 $370, 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

Browse Woolford vacation photos for more inspiration