Woolford Vacation Rentals from $261: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Woolford vacation rentals

1. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

Rochelle K.

$735 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Robert

$366 nightly

Sep 1 - Sep 2

Total with taxes and fees

3. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

$239 nightly

Aug 31 - Sep 1

Total with taxes and fees

4. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

$286 nightly

Sep 29 - Sep 30

Total with taxes and fees

5. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

$451 nightly

Sep 27 - Sep 28

Total with taxes and fees

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

$247 nightly

Sep 2 - Sep 3

Total with taxes and fees

7. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

$520 nightly

Sep 2 - Sep 3

Total with taxes and fees

8. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge

Anonymous traveler

$682 nightly

Aug 31 - Sep 1

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Apartments

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Woolford Hotel Reviews

Quality Inn Solomons - Beacon Marina

10/10 Excellent

"clean room, easy to highway and breakfast great"

St Michaels Inn

8/10 Good

"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"

Holiday Inn Express Cambridge by IHG

8/10 Good

"My room was very clean and spacious. 1st floor room was a bit noisy. The blow dryer was sticky and felt pretty gross. I did mention this to front desk staff, so hopefully they will be cleaning those in a more regular basis. Comfortable bed, nice breakfast and lived that freshly brewed coffee is available at all times in the lobby. Staff was friendly and helpful. Would stay here again. Very convenient location on main highway and a short drive to downtown Cambridge."

Find out more about Woolford

Everything you need to know about Woolford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woolford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woolford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woolford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woolford. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Woolford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $261 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woolford rentals

At Expedia, we put the best Woolford vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Woolford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woolford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woolford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Woolford?

Yes, we offer vacation rentals near well known sights in Woolford, or you can choose a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Woolford?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted: Visitors like this Woolford vacation home rental. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. Our travelers also rate The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks as a favorite home for rent in Woolford.

How many vacation rentals will I find in Woolford?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Woolford stay.

What can I see and do in Woolford?

Blackwater National Wildlife Refuge and Woods Island are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center.

What’s a vacation rental in Woolford like?

A vacation rental is a private property where you can stay for a couple of days or more in Woolford. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.

Room 1

Check prices for these dates

Our top choices for Woolford vacation rentals

1. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

2. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

3. Sailwinds Loft at Cambridge Creek

4. Soul Oasis - home on the Chesapeake Bay

5. Sunset Breezes - quiet waterfront retreat

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

7. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

8. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

9. Family Beach House: Spacious Deck, Grill & Views

10. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

11. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

12. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

13. 4-BR Waterfront Turret Home

14. Plum Point Cottage #17

15. Lakefront Cabin Near Solomons Island w/ Hot Tub

16. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

17. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

Find vacation rentals that suit your style

Top Woolford Hotel Reviews

Quality Inn Solomons - Beacon Marina

St Michaels Inn

The Tilghman Island Inn

Comfort Inn & Suites Lexington Park near Pax River

Holiday Inn Express Cambridge by IHG

Sandaway Suites & Beach

Hampton Inn Easton

Quality Inn

Hilton Garden Inn Solomons

Find out more about Woolford

Frequently asked questions

Woolford Vacation Rentals

Check prices for these dates

Our top choices for Woolford vacation rentals

1. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

2. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

3. Sailwinds Loft at Cambridge Creek

4. Soul Oasis - home on the Chesapeake Bay

5. Sunset Breezes - quiet waterfront retreat

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

7. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

8. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

9. Family Beach House: Spacious Deck, Grill & Views

10. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

11. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

12. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

13. 4-BR Waterfront Turret Home

14. Plum Point Cottage #17

15. Lakefront Cabin Near Solomons Island w/ Hot Tub

16. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

17. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

Find vacation rentals that suit your style

Top Woolford Hotel Reviews

Quality Inn Solomons - Beacon Marina

Find out more about Woolford

Frequently asked questions

7. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8