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Royal Oak Holiday Apartments

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50 rentals in Royal Oak.
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), holiday 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, holiday 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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Charming Waterfront Cottage Outside St. Michaels Close to the Oaks, holiday rental in Royal Oak

Charming Waterfront Cottage Outside St. Michaels Close to the Oaks

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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St. Michael's Waterfront Vacation Home, holiday rental in Royal Oak

St. Michael's Waterfront Vacation Home

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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RESTORED WATERFRONT COTTAGE, holiday rental in Royal Oak

RESTORED WATERFRONT COTTAGE

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes, holiday rental in Royal Oak

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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6942 Travelers Rest, holiday rental in Royal Oak

6942 Travelers Rest

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful Cambridge Home on Jenkins Creek, holiday rental in Royal Oak

Peaceful Cambridge Home on Jenkins Creek

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, holiday rental in Royal Oak

New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, holiday 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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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, holiday 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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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, holiday 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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Newly available rental:  Relaxing Waterfront Cottage Near St Michaels, Maryland, holiday rental in Royal Oak

Newly available rental: Relaxing Waterfront Cottage Near St Michaels, Maryland

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

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Family Retreat with Deepwater Dock, holiday rental in Royal Oak

Waterfront Family Retreat with Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Fully remodel 2 bedroom country cottage., holiday rental in Royal Oak

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Getaway on the Choptank River, holiday rental in Royal Oak

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Sunsets and Chesapeake Charm, holiday rental in Royal Oak

Gorgeous Sunsets and Chesapeake Charm

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Holidays at the Cove  - plenty of space to gather while making memories, holiday 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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My Chesapeake Retreat Cambridge, Maryland, holiday rental in Royal Oak

My Chesapeake Retreat Cambridge, Maryland

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Royal Oak

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, holiday rental in Royal Oak

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, holiday 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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Location Location! St Michaels-- In Town Cottage!, holiday rental in Royal Oak

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Relax in Tilghman Island, holiday rental in Royal Oak

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, holiday rental in Royal Oak

Premier Cottage in St. Michaels- In Town Location!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cottage at Heron Cove, Chesapeake Bay, Cambridge, holiday rental in Royal Oak

Cottage at Heron Cove, Chesapeake Bay, Cambridge

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels, holiday rental in Royal Oak

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, holiday rental in Royal Oak

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious Waterfront Kent Island Home 30 miles from Annapolis, holiday rental in Royal Oak

Luxurious Waterfront Kent Island Home 30 miles from Annapolis

4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Main House at Grandview at Pleasure Point, holiday rental in Royal Oak

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes, holiday 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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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, holiday 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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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday 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, holiday 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!, holiday rental in Royal Oak

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Beatiful Waterfront Home with Large Deck, Pool and Spa close to Bay Bridge, holiday rental in Royal Oak

Beatiful Waterfront Home with Large Deck, Pool and Spa close to Bay Bridge

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., holiday 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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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, holiday 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, holiday 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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Cottage 2 at Grandview Pleasure Point, holiday 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!, holiday 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 Property, Kayaks, Private Dock, Near Town, holiday 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, holiday 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, holiday 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, holiday 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, holiday rental in Royal Oak

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private setting, enjoy nature, kayaking and total relaxation, holiday rental in Royal Oak

Private setting, enjoy nature, kayaking and total relaxation

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private waterfront estate with pool, convenient to Easton and St. Michaels, holiday 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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Bay Cottage Resort, holiday rental in Royal Oak

Bay Cottage Resort

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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