Woolford Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Woolford vacation rentals

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is ¥36,510
¥42,402 total
includes taxes & fees
May 27 - May 28
Waterfront Getaway with Dock

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is ¥22,490
¥47,679 total
includes taxes & fees
May 27 - May 28
Soul Oasis - home on the Chesapeake Bay

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ¥26,986
¥77,307 total
includes taxes & fees
May 19 - May 20
Family Beach House: Spacious Deck, Grill & Views

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (27 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is ¥24,549
¥40,124 total
includes taxes & fees
May 27 - May 28
Sailwinds Loft at Cambridge Creek

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is ¥38,098
¥75,046 total
includes taxes & fees
May 25 - May 26
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is ¥36,510
¥72,185 total
includes taxes & fees
May 19 - May 20
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is ¥33,335
¥68,988 total
includes taxes & fees
May 19 - May 20
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (11 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is ¥35,717
¥71,849 total
includes taxes & fees
May 19 - May 20
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very Good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is ¥30,884
¥61,109 total
includes taxes & fees
May 27 - May 28
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is ¥38,803
¥75,547 total
includes taxes & fees
May 27 - May 28
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is ¥64,914
¥116,823 total
includes taxes & fees
May 27 - May 28
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is ¥42,763
¥51,708 total
includes taxes & fees
May 17 - May 18
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is ¥28,508
¥47,343 total
includes taxes & fees
Jun 9 - Jun 10
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

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

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is ¥45,784
¥89,158 total
includes taxes & fees
May 20 - May 21
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is ¥66,203
¥82,383 total
includes taxes & fees
May 27 - May 28
Sunset Breezes - quiet waterfront retreat

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is ¥87,109
¥155,949 total
includes taxes & fees
May 25 - May 26
4-BR Waterfront Turret Home

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Beach House w/TheaterRm, GameRm, Outdoor Shwr
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"This was a fantastic property and location for our stay in Lusby. The home is designed with families in mind, and there was plenty for everyone to do. The house is beautiful and in a quiet, residential community. You can walk to the beach less than two blocks away, and we found dozens of sharks teeth there! Josh was so helpful with advice throughout. We would definitely come again."
United States
Mollie O.
The price is ¥57,300
¥120,505 total
includes taxes & fees
Jun 1 - Jun 2
Beach House w/TheaterRm, GameRm, Outdoor Shwr

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

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is ¥76,656
¥161,161 total
includes taxes & fees
Jun 2 - Jun 3
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is ¥42,763
¥51,708 total
includes taxes & fees
May 17 - May 18
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is ¥67,628
¥154,962 total
includes taxes & fees
Jun 1 - Jun 2
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Woolford Hotel Reviews

Find out more about Woolford

Search for holiday rentals in Woolford on Expedia! You can easily find your home rentals, villas, holiday apartments in Woolford using one of the methods below:

  • View our selection of featured holiday rentals in Woolford
  • Use the map to find apartments and other holiday homes in the Woolford neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woolford while they last

Look no further and take a look at our great range of rental properties in Woolford!

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?

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: Visitors give good reviews to this Woolford vacation home rental, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.