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Tonight
Check prices in Woolford for tonight, Sep 14 - Sep 15
Sep 14 - Sep 15
Tomorrow night
Check prices in Woolford for tomorrow night, Sep 15 - Sep 16
Sep 15 - Sep 16
This weekend
Check prices in Woolford for this weekend, Sep 18 - Sep 20
Sep 18 - Sep 20
Next weekend
Check prices in Woolford for next weekend, Sep 25 - Sep 27
Sep 25 - Sep 27

Most frequently booked Woolford hotels

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
0.63 km from city centre
The price is CA $599 per night
CA $599
CA $1,062 total
Sep 15 - Sep 16
includes taxes & fees
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, Dock Pet permitted

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

Woolford MD
4.48 km from city centre
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
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
29.69 km from city centre
The price is CA $122 per night
CA $122
CA $134 total
Sep 20 - Sep 21
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
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
13.46 km from city centre
The price is CA $302 per night
CA $302
CA $409 total
Sep 29 - Sep 30
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
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Free cancellation
Reserve now, pay when you stay
31.68 km from city centre
The price is CA $249 per night
CA $249
CA $274 total
Sep 30 - Oct 1
includes taxes & fees
Book a stay at this spa hotel in Easton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Avalon Theatre and Customs House are located nearby.
Spa
Parking included
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
32.16 km from city centre
The price is CA $836 per night
CA $836
CA $920 total
Oct 6 - Oct 7
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
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
Free cancellation
Reserve now, pay when you stay
13.65 km from city centre
The price is CA $100 per night
CA $100
CA $111 total
Sep 16 - Sep 17
includes taxes & fees
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.
Pool
Breakfast included
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
Free cancellation
Reserve now, pay when you stay
31.92 km from city centre
The price is CA $332 per night
CA $332
CA $399 total
Oct 5 - Oct 6
includes taxes & fees
Stay at this hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Higgins Yacht Yard and Marina and Muskrat Park are located nearby.
Breakfast included
Pet-friendly
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Free cancellation
13.98 km from city centre
The price is CA $163 per night
CA $163
CA $181 total
Oct 5 - Oct 6
includes taxes & fees
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Woolford
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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.

Woolford hotels essential information

Accommodation
536 hotels
Lowest Price
CA $111
Highest Price
CA $1,062
Popular hotels
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted, St Michaels Inn, Hyatt Regency Chesapeake Bay, The Tidewater Inn, Inn at Perry Cabin, Days Inn & Suites by Wyndham Cambridge, The Wildset, Comfort Inn & Suites Cambridge

Frequently asked questions

What are the top kid-friendly hotels in Woolford?
From carefully considered amenities to extra room to move, kid-friendly hotels come with features that can help turn a standard family vacation into an incredible one. These Woolford properties make getting away with youngsters a cinch: Your crew will enjoy their time at The Retreat - The Perfect Ambiance!. A playground and animal viewing activities are among the things that help make this property a sought-after option. Alternatively, spend your Woolford escape at Waterfront Getaway with Dock. Take advantage of a playground, animal viewing activities and more here.
Where can I find cheap hotels in Woolford?
At Travelocity you'll find really nice hotels in Woolford at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Woolford rather than in Woolford. We may find you even better rates, too.
How do I find the best Woolford hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Woolford then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Woolford?
The cheapest hotel in Woolford is CA $111 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Woolford?
There are 536 hotels in Woolford on Travelocity.
What are the best hotels in Woolford?
Woolford has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Woolford for you!
When is the best time to visit Woolford?
If you want the joy of a fun-filled trip in peak season, visit Woolford during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Woolford?
Based on historic data is usually the cheapest month to visit Woolford. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Woolford?
There are multiple hotels in Woolford that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Woolford. We have plenty of kid-friendly hotels in Woolford to choose from on Travelocity!
Why book a hotel in Woolford through Travelocity?
Because we have the top hotels in Woolford! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Woolford on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Woolford hotel reviews by fellow wanderers

St Michaels Inn

St Michaels Inn

4 out of 5
Posted 7 hours ago
Travelocity Verified Review
"Staff was super sweet, we had some loud neighbors, pool was still open after Labor Day but it’s out front by the road so not very private."
A verified traveller stayed at St Michaels Inn
St Michaels Inn