Woolford Vacations from $290
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Your Woolford Vacation
Say bye-bye to the stress of planning and hello to a Woolford vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is good for bars and pubs, culture and cafes. In the mood for a bit of sightseeing? A trip to Woolford wouldn't be complete without checking out Harriet Tubman Underground Railroad National Historical Park, Spocott Windmill and other major attractions. Your ideal Woolford vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.
The Latest Woolford vacation packages
Price found within the past 48 hours. Click for updated prices.
Best Western Kent Narrows Inn
Price was $361, price is now $290 per person
$290
per person
Dec 30 - Jan 3
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Salisbury (SBY)
8/10 Very Good! (1,002 reviews)
Staff was courteous. Room was in good condition but “no frills.” Fitness center very small and breakfast was not great. For the money, acceptable.
Reviewed on Nov 23, 2025
Hilton Garden Inn Kent Island Marina
Save 100% on your flight
Price was $532, price is now $380 per person
$380
per person
Dec 30 - Jan 3
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Salisbury (SBY)
9/10 Wonderful! (1,000 reviews)
We’ve stayed here lots of times and we’re always pleased. Clean large rooms, friendly staff and great location
Reviewed on Nov 25, 2025
Studio 6 Suites Pocomoke City, MD
Price was $531, price is now $455 per person
$455
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Salisbury (SBY)
7.6/10 Good! (56 reviews)
Staff was courteous, but slow in directing to a room
that needed a short approach
due to mobility
issues. ,(500 ft exterior walk is not user friendly &mobility challenge. Third time into office for room placement. Lock card did not work,after 1 night,
No toiletries, a bar of soap! No cable print guide. Room amenities very poor. Ads said it had been renovated,but rooms
sure did not look it.
Overall poor communication,but one observant worker noticed people were moving about and opened the free breakfast 30 min early.
Competitor- Red Roof Inn was all that this wasn't.
Reviewed on Nov 9, 2025
Holiday Inn Express Annapolis East-Kent Island by IHG
Price was $360, price is now $309 per person
$309
per person
Dec 30 - Jan 3
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Salisbury (SBY)
9.2/10 Wonderful! (921 reviews)
Hotel is nice. Staff is great. Rooms were nice and clean but the room noise from neighbor was pretty wild. Loud conversations thru the walls woke me up in early morning. The room doors slam like a vault too. Bring a noise machine.
Reviewed on Nov 22, 2025
Woolford Hotel Deals
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford MD
9.8/10 Exceptional! (58 reviews)
We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family.
Reviewed on Aug 24, 2025
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
9.4/10 Exceptional! (21 reviews)
House was wonderful, it had something for all ages, plenty of room for our group of 17. We also had family that lived nearby by over for breakfast one morning and still plenty of room. Lots of utensils for all our cooking needs. House was very clean. Host was very responsive with a couple of questions ...
Reviewed on Oct 20, 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$201 nightly
The price is $229 total per night from Dec 2 to Dec 3
$229 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
Staff was fantastic, and although it was cooler due to the fall weather, there was still quite a few activities., Especially if you golf. Overall, slightly overpriced for the off-season in Cambridge, but clearly on point for warmer weather.
Reviewed on Nov 22, 2025
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.
Find the Best Woolford Vacation Packages
Woolford Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Bill Burton Fishing Pier State Park, Choptank River Lighthouse and Great Marsh Park |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
