Find hotels in Woolford, MD from $72

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Compare 505 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (8)
"We had a wonderful time! The house was super cute and clean. The views off the water in the morning and the evening were beautiful! All of the blackout shades came in very handy for our baby and little ones who sleep better in darker rooms. The hot tub was magical and taking the kayaks out onto the water was so fun! Only recommendation would be to bring bug spray! Thanks for a wonderful stay. We would love to come back."
The price is $382
$679 total
includes taxes & fees
May 30 - May 31
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Indoor pool and spa in contemporary French home secluded in surrounding woods
Interior
Indoor pool and spa in contemporary French home secluded in surrounding woods
10.0 out of 10, Exceptional, (9)
"Highly recommend this home. All the amenities you’ll ever need in a peaceful and private setting yet still so close to the beach and much more. The indoor pool and spa are even better than the pictures. Also have to note the owners take excellent care of the property and it shows. If you’re on the fence about booking do not hesitate."
Indoor pool and spa in contemporary French home secluded in surrounding woods
Guest Quarters at the Inn - 102
1 bedroom, iron/ironing board, free WiFi, bed sheets
Guest Quarters at the Inn - 102
10.0 out of 10, Exceptional, (15)
"Really enjoyed the location of this property, and how quiet it was at all hours. WiFi was fast enough for video calls and streaming. Comfy beds, too."
Guest Quarters at the Inn - 102
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The Blue Crab Beach House - Free beach passes
Beach nearby, sun loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Maryland Vacation Rental w/ Private Pool & Dock
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (3)
"Loved the house and kids loved the pool. We also managed to catch a half dozen crabs (August trip). House is on the smaller side, but with four bedrooms everyone had privacy and just what they needed. We'll be back!"
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (25)
"Three of us stayed overnight on a girl's weekend visit to Blackwater. This property is beautiful! Sunrise over the water was amazing. The house was spotless, stocked with everything you need right down to shower products. The furniture is very comfortable, beds are as well. We didn't get to use the screened porch as it was too chilly, but it will be great in warmer weather. The chickens had a lot to say in the morning, so I felt obligated to stop and visit for a bit. Will definitely stay here...
The price is $220
$263 total
includes taxes & fees
May 5 - May 6
Waterfront Getaway with Dock
The Tilghman Island Inn
Garden View Double Queen First Level - Not Dog Friendly | View from room
The Tilghman Island Inn
3.5 star property
9.8 out of 10, Exceptional, (48)
"This hotel/inn was perfect. Our stay was amazing. I proposed to my now fiancé and the hotel helped me plan and helped with the room to celebrate. The staff is super sweet and very hospitable. We had a lovely time and will come back in the near future!"
The price is $265
$292 total
includes taxes & fees
May 19 - May 20
The Tilghman Island Inn
Guest Quarters at the Inn - 103
Iron/ironing board, free WiFi, bed sheets
Guest Quarters at the Inn - 103
9.8 out of 10, Exceptional, (21)
"Quaint, quiet, clean, and close to restaurants and our wedding venue we attended. Would return and recommend! Thank you!"
Guest Quarters at the Inn - 103
Harbor Breezes at Herrington Harbor
Property grounds
Harbor Breezes at Herrington Harbor
9.8 out of 10, Exceptional, (28)
"Rented the house to attend my daughter’s wedding. House was to be for, wife and I, in-laws, my mother and my son. House was great, clean, well kept, bed’s comfortable, great location. Only issue, it is not a four bedroom, it is three and a sofa bed in the living room. Post said common area. I had to get a hotel room to accommodate my adult son at the last minute."
Harbor Breezes at Herrington Harbor
The Middle Point Cabin in Saint Michaels
Property grounds
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Charming and Private with a Water view
Exterior
Charming and Private with a Water view
9.6 out of 10, Exceptional, (25)
"I stayed here with my husband in August 2023. We had a great time! Sitting outside you can see hummingbirds, eagles, cardinals, and more. But be sure to bring bug spray because the mosquitoes are relentless. The house is fully stocked with everything you need, such as toilet paper, napkins, kitchenware, towels, etc. We had breakfast at Cindy’s cafe a couple times, a local favorite, and it was delicious. If you want a casual lunch/dinner go to Carmela’s for excellent pizza and Italian food. There...
Charming and Private with a Water view
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Beach nearby
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (34)
"Clean! Great location. Easy check in"
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Guest Quarters at the Inn - 101
Iron/ironing board, free WiFi, bed sheets
Guest Quarters at the Inn - 101
9.6 out of 10, Exceptional, (10)
"The location of this room is perfect for your stay in North Beach! Walking distance to the beach/boardwalk, several stores, restaurants, coffee shop, and beer garden. The included beach pass was so helpful! The check-in, check-out process was so easy. Our only complaint was the noise from the guests in the room above us and you could hear the live music from the nearby beer garden until 10:30 pm - however, the positives FAR outweighed the noise."
Guest Quarters at the Inn - 101
Welcome to Hickory House on the Chesapeake Bay!
Beach nearby, sun loungers, beach towels
Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (19)
"Had a great week! Cottage is adorable, clean and cozy. Host very welcoming with treats and bowls for our dogs. House is a couple weeks from the beach and a beach parking pass is included. The beach is private and very relaxing. It was very hot that week that we visited abd tge AC was excellent. Lots of extras in the house - games, hand soaps and even ballth salts! Very enjoyable visit!"
Welcome to Hickory House on the Chesapeake Bay!
Shewell's Townhouse in Prince Frederick
Fridge, microwave, oven, stovetop
Shewell's Townhouse in Prince Frederick
9.6 out of 10, Exceptional, (11)
"Shewells townhouse worked great for our stay in Prince Frederick. It was close to everything we needed during our stay. We would definitely use this property again for a trip to southern Maryland should the opportunity arise."
Shewell's Townhouse in Prince Frederick
Knapps Narrows Marina & Inn
Exterior
Knapps Narrows Marina & Inn
3.0 star property
9.4 out of 10, Exceptional, (302)
"Super friendly staff at check in. Gorgeous view. Great stay. "
The price is $210
$231 total
includes taxes & fees
May 5 - May 6
Knapps Narrows Marina & Inn
Cute Bay Home/Fantastic View and Sandy Beach
Fridge, microwave, oven, stovetop
Cute Bay Home/Fantastic View and Sandy Beach
9.4 out of 10, Exceptional, (23)
"Wonderful experience at this amazing house. Love this little community and the beach is right there! Would definitely stay again!!! Thank you!"
Cute Bay Home/Fantastic View and Sandy Beach
Hideaway By The Bay - Sunroom, bay view, propane fire pit, 6ft tall wood fence
Property grounds
Hideaway By The Bay - Sunroom, bay view, propane fire pit, 6ft tall wood fence
9.2 out of 10, Wonderful, (11)
"Home has a great feel to it, and the owner is incredibly responsive; we struck up a genuine friendship. I would definitely rent again."
The price is $240
$412 total
includes taxes & fees
May 31 - Jun 1
Hideaway By The Bay - Sunroom, bay view, propane fire pit, 6ft tall wood fence
Black Walnut Point Inn
Outdoor pool
Black Walnut Point Inn
3.5 star property
9.0 out of 10, Wonderful, (53)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
The price is $178
$196 total
includes taxes & fees
May 12 - May 13
Black Walnut Point Inn
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See all available properties in Woolford
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.

More cheap stays in Woolford

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2936 Ocean Gtwy, Cambridge, MD
The price is $99 per night from May 5 to May 6
$99
$110 total
includes taxes & fees
May 5 - May 6
8/10 Very Good! (626 reviews)

Woolford Travel Info

Number of reviews
4,199
Accommodation
505 hotels
Highest price
$382
Lowest price
$72
Reasons to visit
Choptank River Lighthouse, Great Marsh Park and Long Wharf Park

Frequently asked questions

What's the best place for a stay in Woolford?

Based on Expedia's traveler preferences, Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April is a top place to stay in Woolford. Two other options for your trip to the area are Hyatt Regency Chesapeake Bay and St Michaels Inn. See all available top hotels, or vacation rentals in Woolford.

What are some of the best vacation rentals that Woolford has to offer?

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: This vacation home rental outside Woolford is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Woolford.

If I need to cancel my hotel reservation in Woolford, will I receive a refund?

Yes! The majority of hotel reservations are fully refundable as long as you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Woolford.

Where can I learn more about changing or cancelling my trip to Woolford?

For more information about rescheduling or cancelling your trip to Woolford, click here.

What are some hotels with pools in Woolford?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock - Free Night thru April: Features a sauna, a pool, and sun loungers. Hyatt Regency Chesapeake Bay and St Michaels Inn are two additional hotels that feature an onsite pool. View all hotels with pools in Woolford.

What is staying in Woolford like?

Travelers to Woolford will find plenty to explore and enjoy. In Woolford, there are 9 hotels and other accommodations to choose from. Find out more about Woolford.

What are the top places to visit in Woolford?

A favorite place to visit is Blackwater National Wildlife Refuge. You'll also find Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center in the area. Check out what more to see and do in Expedia's Woolford guide.

What's the weather like in Woolford?

The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for Woolford is 48 inches.

Recent reviews of Woolford hotels
Expedia verified reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

5/5 Excellent
"This was our 6 time visiting the resort. We love everything about the place. The only concern we have is the parking. We have 2 sons with Down Syndrome, so it would be nice if there was handica parking a little closer to the hotel."
A verified traveler stayed at Hyatt Regency Chesapeake Bay
Posted 3 days ago
Hyatt Regency Chesapeake Bay