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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Royal Oak holiday homes

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

1. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is £295
includes taxes & fees
28 Sept - 29 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

2. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is £493
includes taxes & fees
5 Oct - 6 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

3. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is £197
includes taxes & fees
7 Sept - 8 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lighthouse with a white exterior, a balcony, and a metal roof.

4. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is £206
includes taxes & fees
7 Sept - 8 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
A deck with outdoor furniture, a red door, and a house with siding.

5. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is £197
includes taxes & fees
9 Sept - 10 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

6. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is £247
includes taxes & fees
7 Sept - 8 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

7. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is £315
includes taxes & fees
4 Oct - 5 Oct
Sunset Breezes - quiet waterfront retreat

8. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is £331
includes taxes & fees
7 Sept - 8 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

9. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is £346
includes taxes & fees
14 Sept - 15 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

10. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is £309
includes taxes & fees
7 Sept - 8 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A beach with chairs and a pier in the background.

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is £369
includes taxes & fees
9 Sept - 10 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A spacious living room with a large TV, blue sofa, and a ceiling fan.

12. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Anne is a great host, always responded promptly regardless of time.Property is huge! Lots of patio space, and included kayaks for us to use. Next time in the area will definitely stay there"
United States
Ramon A.
The price is £561
includes taxes & fees
13 Sept - 14 Sept
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

13. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is £335
includes taxes & fees
18 Sept - 19 Sept
Plum Point Cottage #17
A wooden interior with a dining area, sofas, and a table.

14. 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
9.0 out of 10, Wonderful, (14 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is £538
includes taxes & fees
5 Oct - 6 Oct
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

15. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is £423
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

16. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is £390
includes taxes & fees
10 Sept - 11 Sept
3-bedroom house in Deale located on Bay many amenities and great views
A sign for Herrington Harbour with a clear sky and parked cars in the background.

17. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
The price is £349
includes taxes & fees
5 Oct - 6 Oct
Rose Haven Coastal Cottage
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

18. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is £579
includes taxes & fees
8 Sept - 9 Sept
Charming Annapolis WaterVIEW Home
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

19. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is £1,002
includes taxes & fees
7 Sept - 8 Sept
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A two-story house with a red roof, a brick chimney, and a small porch.

20. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is £771
includes taxes & fees
8 Sept - 9 Sept
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
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.
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Top Royal Oak Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"We loved everything about this place. The view from the pool of the Choptank River was absolutely stunning."
Naomi 2-night trip
Posted less than an hour ago
Hyatt Regency Chesapeake Bay

Find out more about Royal Oak

Royal Oak Holiday Homes information

Number of reviews
339
Accommodation
355 Holiday Homes
Lowest Price
£197
Highest Price
£1,002