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Woolford Holiday Rentals

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50 rentals in Woolford.
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Waterfront Family Retreat with Pool on 7+ acres!, holiday rental in Woolford

Waterfront Family Retreat with Pool on 7+ acres!

10 bedrooms
7 bathrooms
Sleeps 24
Match: Sleeps
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Peaceful Cambridge Home on Jenkins Creek, holiday rental in Woolford

Peaceful Cambridge Home on Jenkins Creek

3 bedrooms
2 bathrooms
Sleeps 7
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), holiday rental in Woolford

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

7 bedrooms
9 bathrooms
Sleeps 20
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Family and Pet-Friendly, Waterfront with Pier, holiday rental in Woolford

Family and Pet-Friendly, Waterfront with Pier

4 bedrooms
2 bathrooms
Sleeps 8
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, holiday rental in Woolford

Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay, holiday rental in Woolford

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, holiday rental in Woolford

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
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St. Michael's Waterfront Vacation Home, holiday rental in Woolford

St. Michael's Waterfront Vacation Home

5 bedrooms
5 bathrooms
Sleeps 12
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Fully remodel 2 bedroom country cottage., holiday rental in Woolford

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A Vacation Away From It All-Family And Pet Friendly, holiday rental in Woolford

A Vacation Away From It All-Family And Pet Friendly

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront Rental on Fishing Creek, Cambridge, MD, holiday rental in Woolford

Waterfront Rental on Fishing Creek, Cambridge, MD

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL, holiday rental in Woolford

BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL

4 bedrooms
2 bathrooms
Sleeps 10
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Waterfront Family Retreat with Deepwater Dock, holiday rental in Woolford

Waterfront Family Retreat with Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 15
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, holiday rental in Woolford

Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing

4 bedrooms
5 bathrooms
Sleeps 8
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Relax in Tilghman Island, holiday rental in Woolford

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront, 23 Private Acres, Dock  & Pool, holiday rental in Woolford

Waterfront, 23 Private Acres, Dock & Pool

4 bedrooms
5 bathrooms
Sleeps 17
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Waterfront Retreat on the Chesapeake, holiday rental in Woolford

Waterfront Retreat on the Chesapeake

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, holiday rental in Woolford

Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island

4 bedrooms
2 bathrooms
Sleeps 14
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Vintage Eastern Shore Retreat, holiday rental in Woolford

Vintage Eastern Shore Retreat

4 bedrooms
3 bathrooms
Sleeps 10
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, holiday rental in Woolford

Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton

5 bedrooms
4 bathrooms
Sleeps 10
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Waterfront Getaway on the Choptank River, holiday rental in Woolford

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Victorian Home In Historic West End, holiday rental in Woolford

Victorian Home In Historic West End

6 bedrooms
3 bathrooms
Sleeps 13
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Cottage at Heron Cove, Chesapeake Bay, Cambridge, holiday rental in Woolford

Cottage at Heron Cove, Chesapeake Bay, Cambridge

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Year Round Estate on Bay / Fam. Reunions / Slps 28, holiday rental in Woolford

Year Round Estate on Bay / Fam. Reunions / Slps 28

7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, holiday rental in Woolford

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Main House at Grandview at Pleasure Point, holiday rental in Woolford

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 9
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Little Farmhouse by the bay, holiday rental in Woolford

Little Farmhouse by the bay

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Chesapeake Waterfront Retreat with Pool, holiday rental in Woolford

Chesapeake Waterfront Retreat with Pool

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., holiday rental in Woolford

Not to early to think about joining us this Spring and Summer.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quarterdeck at Swan Cove Manor, holiday rental in Woolford

Quarterdeck at Swan Cove Manor

1 bedroom
1 bathroom
Sleeps 4
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Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, holiday rental in Woolford

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Best kept secret by the bay (Entire House), holiday rental in Woolford

Best kept secret by the bay (Entire House)

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Outrigger at Swan Cove Manor, holiday rental in Woolford

Outrigger at Swan Cove Manor

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge, holiday rental in Woolford

Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cambridge Waterfront Home, holiday rental in Woolford

Cambridge Waterfront Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, holiday rental in Woolford

CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16

5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Spring Is Here, Come Explore Fossils and One Mile of Beach, holiday rental in Woolford

Spring Is Here, Come Explore Fossils and One Mile of Beach

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cottage 2 at Grandview Pleasure Point, holiday rental in Woolford

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, holiday rental in Woolford

Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in Woolford

Waterfront Property, Kayaks, Private Dock, Near Town

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quiet cottage on wooded property, holiday rental in Woolford

Quiet cottage on wooded property

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage 1a at Grandview Pleasure Point, holiday rental in Woolford

Cottage 1a at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point, holiday rental in Woolford

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina, holiday rental in Woolford

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Business or Leisure?, holiday rental in Woolford

Business or Leisure?

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Hoopersville Getaway on Chesapeake Bay!, holiday rental in Woolford

Historic Hoopersville Getaway on Chesapeake Bay!

7 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Cambridge Colonial Home, Walk to Town & Waterfront, holiday rental in Woolford

Cambridge Colonial Home, Walk to Town & Waterfront

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Beautiful Colonial Home on the Choptank River, holiday rental in Woolford

NEW! Beautiful Colonial Home on the Choptank River

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Cozy Cottage w/Yard < .2 Mi to Choptank River, holiday rental in Woolford

NEW! Cozy Cottage w/Yard < .2 Mi to Choptank River

4 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Mariner at Swan Cove Manor, holiday rental in Woolford

Mariner at Swan Cove Manor

5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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