We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Royal Oak Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
50 rentals in Royal Oak.
Sort by:
Tripadvisor Sort
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Royal Oak rentals sent straight to your email!
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
More info
Vrbo.com logo
Check-in
Check-out
Relax in Tilghman Island, holiday rental in Royal Oak

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Check-in
Check-out
Payment Protection
Victorian Home In Historic West End, holiday rental in Royal Oak

Victorian Home In Historic West End

6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
*****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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
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
More info
Vrbo.com logo
Check-in
Check-out
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Royal Oak

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

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out
Quarterdeck at Swan Cove Manor, holiday rental in Royal Oak

Quarterdeck at Swan Cove Manor

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
Waterview Cottage In St. Michaels!, holiday rental in Royal Oak

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
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
More info
Vrbo.com logo
Check-in
Check-out
Outrigger at Swan Cove Manor, holiday rental in Royal Oak

Outrigger at Swan Cove Manor

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, holiday 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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, holiday 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
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
Tranquil Easton Waterfront Property, holiday rental in Royal Oak

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
Cambridge Colonial Home, Walk to Town & Waterfront, holiday rental in Royal Oak

Cambridge Colonial Home, Walk to Town & Waterfront

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
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
More info
Check-in
Check-out
Payment Protection
Bay Cottage Resort, holiday rental in Royal Oak

Bay Cottage Resort

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Wye Island View, holiday rental in Royal Oak

Tentrr Signature Site - Wye Island View

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Mariner at Swan Cove Manor, holiday rental in Royal Oak

Mariner at Swan Cove Manor

5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PreviousNext
1
Frequently Asked Questions about Royal Oak