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Royal Oak Vacation Rentals

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50 rentals in Royal Oak.
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), vacation rental in Royal Oak

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

7 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, vacation rental in Royal Oak

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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St. Michael's Waterfront Vacation Home, vacation rental in Royal Oak

St. Michael's Waterfront Vacation Home

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Peaceful Cambridge Home on Jenkins Creek, vacation rental in Royal Oak

Peaceful Cambridge Home on Jenkins Creek

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, vacation rental in Royal Oak

TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, vacation rental in Royal Oak

Comfy home on beautiful Leadenham Creek. Book now for summer!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Fully remodel 2 bedroom country cottage., vacation rental in Royal Oak

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Family Retreat with Deepwater Dock, vacation rental in Royal Oak

Waterfront Family Retreat with Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, vacation rental in Royal Oak

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

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, vacation rental in Royal Oak

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Royal Oak

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Relax in Tilghman Island, vacation rental in Royal Oak

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Royal Oak

Holidays at the Cove - plenty of space to gather while making memories

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Getaway on the Choptank River, vacation rental in Royal Oak

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Retreat on the Chesapeake, vacation rental in Royal Oak

Waterfront Retreat on the Chesapeake

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, vacation rental in Royal Oak

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

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, vacation rental in Royal Oak

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, vacation rental in Royal Oak

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Cottage at Heron Cove, Chesapeake Bay, Cambridge, vacation rental in Royal Oak

Cottage at Heron Cove, Chesapeake Bay, Cambridge

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Victorian Home In Historic West End, vacation rental in Royal Oak

Victorian Home In Historic West End

6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, vacation rental in Royal Oak

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, vacation rental in Royal Oak

Premier Cottage in St. Michaels- In Town Location!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels, vacation rental in Royal Oak

*****Waterfront home w/ pool in St. Michaels

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Main House at Grandview at Pleasure Point, vacation rental in Royal Oak

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, vacation rental in Royal Oak

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes, vacation rental in Royal Oak

Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, vacation rental in Royal Oak

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Private waterfront estate with pool, convenient to Easton and St. Michaels, vacation rental in Royal Oak

Private waterfront estate with pool, convenient to Easton and St. Michaels

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Quarterdeck at Swan Cove Manor, vacation rental in Royal Oak

Quarterdeck at Swan Cove Manor

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, vacation rental in Royal Oak

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, vacation rental in Royal Oak

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterview Cottage In St. Michaels!, vacation rental in Royal Oak

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., vacation rental in Royal Oak

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Outrigger at Swan Cove Manor, vacation rental in Royal Oak

Outrigger at Swan Cove Manor

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, vacation rental in Royal Oak

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, vacation rental in Royal Oak

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, vacation rental in Royal Oak

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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Cottage 2 at Grandview Pleasure Point, vacation rental in Royal Oak

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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St. Michael's Premier in Town Summer Cottage!, vacation rental in Royal Oak

St. Michael's Premier in Town Summer Cottage!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, vacation rental in Royal Oak

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, vacation rental in Royal Oak

Waterfront Property, Kayaks, Private Dock, Near Town

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cottage 1a at Grandview Pleasure Point, vacation rental in Royal Oak

Cottage 1a at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point, vacation rental in Royal Oak

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tranquil Easton Waterfront Property, vacation rental in Royal Oak

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in Royal Oak

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cambridge Colonial Home, Walk to Town & Waterfront, vacation rental in Royal Oak

Cambridge Colonial Home, Walk to Town & Waterfront

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Private setting, enjoy nature, kayaking and total relaxation, vacation rental in Royal Oak

Private setting, enjoy nature, kayaking and total relaxation

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bay Cottage Resort, vacation rental in Royal Oak

Bay Cottage Resort

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Wye Island View, vacation rental in Royal Oak

Tentrr Signature Site - Wye Island View

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Mariner at Swan Cove Manor, vacation rental in Royal Oak

Mariner at Swan Cove Manor

5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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