Top 10 Hotels in Woolford, MD from SAR 297 - Competitive Prices

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Our top choices for Woolford hotels

Woolford

Signature Room, Courtyard View | Laptop workspace, WiFi (free)

1. Historic 1825 Chesapeake Farm Stay

St. Leonard

SAR 484 total

includes taxes & fees

6 Sep - 7 Sep

2. Marvel's on the Creek

East New Market

Richard

SAR 784 total

includes taxes & fees

11 Aug - 12 Aug

3. Comfort Inn & Suites Cambridge

Cambridge

Stephanie

SAR 481 total

includes taxes & fees

30 Aug - 31 Aug

Premium bedding, desk, iron/ironing board, cribs (free)

4. Days Inn & Suites by Wyndham Cambridge

Cambridge

jannice

SAR 297 total

includes taxes & fees

6 Sep - 7 Sep

5. Cambridge Inn

Cambridge

Chris

SAR 312 total

includes taxes & fees

11 Aug - 12 Aug

Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers

6. Hyatt Regency Chesapeake Bay

Cambridge

Sinan

SAR 1,117 total

includes taxes & fees

24 Aug - 25 Aug

7. Holiday Inn Express Cambridge by IHG

Cambridge

Philip

SAR 563 total

includes taxes & fees

20 Aug - 21 Aug

8. Econo Lodge Easton Route 50

Easton

michael

SAR 335 total

includes taxes & fees

13 Aug - 14 Aug

9. Hampton Inn Easton

Easton

Donald

SAR 604 total

includes taxes & fees

9 Aug - 10 Aug

10. Hummingbird Inn

Easton

Lewis

SAR 1,310 total

includes taxes & fees

18 Aug - 19 Aug

11. The Tidewater Inn

Easton

Diana

SAR 688 total

includes taxes & fees

11 Aug - 12 Aug

12. Sandaway Suites & Beach

Oxford

Rob

SAR 1,121 total

includes taxes & fees

3 Sep - 4 Sep

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

13. The Oaks Waterfront

Easton

Jeffrey

SAR 1,818 total

includes taxes & fees

11 Aug - 12 Aug

14. St Michaels Inn

St. Michaels

Karen

SAR 353 total

includes taxes & fees

23 Aug - 24 Aug

Premium bedding, down comforters, in-room safe, desk

15. Inn at Perry Cabin

Downtown St. Michaels

Michel

SAR 2,565 total

includes taxes & fees

23 Aug - 24 Aug

16. The Wildset

Downtown St. Michaels

Tracey

SAR 1,081 total

includes taxes & fees

19 Aug - 20 Aug

17. George Brooks House B&B

St. Michaels

Erin

SAR 874 total

includes taxes & fees

17 Aug - 18 Aug

18. Knapps Narrows Marina & Inn

Sherwood

BARBARA

SAR 620 total

includes taxes & fees

9 Aug - 10 Aug

19. Wylder Tilghman Island

Tilghman

Leslie

SAR 1,294 total

includes taxes & fees

2 Sep - 3 Sep

20. The Tilghman Island Inn

Tilghman

Wm

SAR 929 total

includes taxes & fees

9 Aug - 10 Aug

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Stay near popular Woolford attractions

Woods Island

Commune with nature and explore the great outdoors at Woods Island during your travels in Woolford.

See properties

Learn more about Woolford

Head to sights like Blackwater National Wildlife Refuge and Woods Island as you discover Woolford.

See all hotels in Woolford

A group of white birds flying over a field of dry grass.

Top Woolford Hotel Reviews

Hilton Garden Inn Solomons

8/10 Good

"Overall the stay was a bit disappointing. All the computers were down on the day of Check-in (Friday July 31 2026) so it was a VERY long wait to get into my two already reserved, pre-paid for rooms. Staff seemed mostly unbothered & wasn’t really talking much to the guests waiting, which was a bit frustrating. I have to mention that the lobby area was extremely hot & didn’t seem to have much AC going, which made it all more miserable. I assume the computer system starting working again later that night as I was called by the front desk staff around 10:00pm to confirm which of my “party” were in which room (although I watched them write it down when we were finally issued our room keys cards) & then I was called again at 10:30pm to request I come down to put a credit card in the system, understandable that a card needs to be on file, but I was traveling with two very young children so to call my room that late and wake everyone up twice was absolutely ridiculous. Later the next night I needed an extra roll of toilet paper, no one was at the front desk, I called out a “Hello”, but got no answer. After roughly 10 minutes the front desk phone rang then a staff member magically appeared from the back area. The water pressure of the shower was horrible & actually cut out more than once during my shower. The “breakfast buffet” was high priced & looked un-appetizing. All that being said the only positives were the common areas & our rooms were clean upon arrival. Would not stay again."

The Oaks Waterfront

10/10 Excellent

"The Oaks Waterfront was exactly the kind of getaway we were looking for. Tucked away in a quiet, secluded setting, it feels like you’re escaping from everything, yet St. Michaels is only a short ride away thanks to their beautiful shuttle. It really gives you the best of both worlds. What stood out most to us was the family-owned and operated feel. Everyone was genuinely friendly, and there was a warmth about the property that made it feel less like a hotel and more like staying with incredibly hospitable friends. It has a relaxed, welcoming atmosphere that makes it easy to settle in. We stayed in one of the cottages, and it was beautifully appointed with comfortable bedding and thoughtful touches that made it feel luxurious without trying too hard. The entire property is impeccably maintained, and you can tell the owners take great pride in every detail. We also traveled with our two dogs, and they were just as welcome as we were. They loved the cottage, and we appreciated the dog beds, bowls, and bottled water waiting for them. Those little touches made all the difference. The food was fresh and delicious, and the complimentary breakfast each morning was another example of the attention to detail they put into the guest experience. A special thank you to Kathie, Brad, Linda, and the entire team, including housekeeping. Their kindness and genuine hospitality are what make The Oaks such a special place."

The Tilghman Island Inn

8/10 Good

"Just left Tilghman Island Inn after a a girl's trip stay. We had the best time. The grounds are beautiful, the room was cleam, bed was comfortable, the pool was so nice, and the morning pastries are delicious. We only wished we had a refrigerator in the room BUT it didn't really matter too much since we were close to the lounge and it was not a busy week. We would recommend this place to anyone and plan to come back again at some point."

The Tidewater Inn

8/10 Good

"The location was great and property was very well kept and accommodating. Staff was very friendly and helpful. Had a great dinner at restaurant on property. Room was comfortable but bathroom very tight with no counter space for use of toiletries. I know it is a historic property with limited space but that would be on my wish list to make getting ready much easier!"

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10/10 Excellent

"We you this place for the groomsmen’s house and it was perfect! They allow multiple cars to be parked I. The driveway which is super helpful especially when you have multiple people coming from different places. The kitchen and table was excellent we were able to sit everyone around the table and enjoy brunch! I would definitely recommend!"

More cheap stays in Woolford

Days Inn & Suites by Wyndham Cambridge

2917 Ocean Gateway Cambridge MD

SAR 268

SAR 297 total

6 Sep - 7 Sep

includes taxes & fees

Frequently asked questions

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

St Michaels Inn, located 18.4 mi (29.7 km) from the heart of Woolford, is a top choice for your stay based on our traveler data. Two other options for your trip to the area are Hyatt Regency Chesapeake Bay and Inn at Perry Cabin. See all available top hotels, or vacation rentals in Woolford.

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

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This vacation home rental outside of Woolford is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games. 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?

St Michaels Inn: Provides daily, a seasonal outdoor pool, and free self parking. Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted and Hyatt Regency Chesapeake Bay 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 couple of favorite places to visit are Blackwater National Wildlife Refuge and Woods Island. 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.

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Our top choices for Woolford hotels

1. Historic 1825 Chesapeake Farm Stay

2. Marvel's on the Creek

3. Comfort Inn & Suites Cambridge

4. Days Inn & Suites by Wyndham Cambridge

5. Cambridge Inn

6. Hyatt Regency Chesapeake Bay

7. Holiday Inn Express Cambridge by IHG

8. Econo Lodge Easton Route 50

9. Hampton Inn Easton

10. Hummingbird Inn

11. The Tidewater Inn

12. Sandaway Suites & Beach

13. The Oaks Waterfront

14. St Michaels Inn

15. Inn at Perry Cabin

16. The Wildset

17. George Brooks House B&B

18. Knapps Narrows Marina & Inn

19. Wylder Tilghman Island

20. The Tilghman Island Inn

Stay near popular Woolford attractions

Woods Island

Learn more about Woolford

Top Woolford Hotel Reviews

Hilton Garden Inn Solomons

More cheap stays in Woolford

Days Inn & Suites by Wyndham Cambridge

Frequently asked questions

Go further with the Expedia app