Royal Oak Holiday Homes
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Holiday Homes in Royal Oak

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Our top choices for Royal Oak holiday homes

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

An aerial view of a marina with numerous boats docked, surrounded by residential and commercial buildings.

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

1. 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)

9.8/10

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."

Dawn G.

The price is AU$440

AU$440

includes taxes & fees

5 Oct - 6 Oct

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

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

A living room with a sofa, a dining table with placemats, a basket of oranges, and a staircase.

A brick building with a white porch and a well-maintained lawn.

An outdoor dining area with wooden tables and chairs, surrounded by greenery and a large tree.

2. 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)

9.4/10

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."

Robert

The price is AU$537

AU$537

includes taxes & fees

27 Oct - 28 Oct

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

A bedroom with a bed, a dresser, a mirror, and a window with curtains.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, a dishwasher, a stove, and a trash can.

A living room with two brown leather sofas, a wooden side table with a lamp, a small shelf with plants, and a painting of a tree.

A dining area with a round table, white chairs, a vase with flowers, and artwork on the wall.

3. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!

Cambridge

The price is AU$558

AU$558

includes taxes & fees

30 Sept - 1 Oct

More, than just a place to sleep - welcome home!

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

A bedroom with a bed, a ceiling fan, a window, and a view of the outdoors.

A single-story house with a front porch, a chimney, and a green door.

A spacious living area with a white sofa, a dining table, and a kitchen with white cabinets.

4. 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)

10/10

Exceptional

(16 reviews)

"very serene, peaceful home on the bay! Amazing getaway! "

Jill C.

The price is AU$830

AU$830

includes taxes & fees

30 Sept - 1 Oct

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

A lighthouse with a white exterior, a balcony, and a metal roof.

A bedroom with a wooden floor, a bed with a white and yellow bedspread, a nightstand, and a window with a view of the outdoors.

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

5. 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)

9.8/10

Exceptional

(47 reviews)

"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"

Michelle P.

The price is AU$437

AU$437

includes taxes & fees

4 Oct - 5 Oct

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

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

A living room with a blue sofa, a round mirror, and a coffee table.

A dining table set with pink bowls and glasses, surrounded by chairs, with a large plant and a window in the background.

A shelf with various potted plants and storage boxes.

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, (24 reviews)

10/10

Exceptional

(24 reviews)

"Cute, family friendly home. Had everything we needed for a comfortable stay."

Johanna S.

The price is AU$485

AU$485

includes taxes & fees

4 Oct - 5 Oct

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

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

A two-story house with a porch, a white picket fence, and blooming pink trees.

A dining area with a wooden table and chairs, a patterned rug, and a staircase leading to another level.

A pier with a wooden walkway, a sandy beach, and a dog on a leash.

7. 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)

10/10

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!!"

Penny N.

The price is AU$524

AU$524

includes taxes & fees

30 Sept - 1 Oct

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

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

A covered grill, a brick pathway, and a patio area with a chair and a table.

A compact kitchen with a dining area, a fireplace, and a ceiling fan.

A white house with a large lawn and a bird sculpture on a pedestal.

8. Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford

10.0 out of 10, Exceptional, (67 reviews)

10/10

Exceptional

(67 reviews)

"It was perfect for our overnight on way to NY!"

Meagan G.

The price is AU$354

AU$354

includes taxes & fees

4 Oct - 5 Oct

Waterfront Getaway with Dock

A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

A multi-story building with a central staircase, outdoor seating area, and potted plants.

A modern kitchen with white cabinets, a marble island, and wooden bar stools.

A spacious living room with a blue wall, wooden flooring, a glass display cabinet, and a dining area with a table and chairs.

9. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat

Dorchester County

10.0 out of 10, Exceptional, (45 reviews)

10/10

Exceptional

(45 reviews)

"Comfortable, roomy, awesome views!"

John C.

Sunset Breezes - quiet waterfront retreat

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

A bedroom with two single beds, a television on a small table, and a white door.

A single-story house with a brick foundation and a flat roof.

A kitchen with wooden cabinets, a black refrigerator, a microwave on a wooden shelf, and a sink with a faucet.

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)

9.6/10

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. "

Robin

The price is AU$770

AU$770

includes taxes & fees

30 Sept - 1 Oct

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

A spacious living room with a large TV, blue sofa, and a ceiling fan.

A long dining table with white chairs, a chandelier, and a wooden floor.

A room with large windows, two blue chairs, a white table, and a lamp.

A modern kitchen with stainless steel appliances, wooden countertops, and a dog lying on the floor.

11. 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)

9.6/10

Exceptional

(35 reviews)

"Beautiful piece of property and clean, comfortable accommodations! Would definitely return if plan to be in that area again!!"

Joyce F.

The price is AU$938

AU$938

includes taxes & fees

7 Oct - 8 Oct

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

12. 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)

9.2/10

Wonderful

(7 reviews)

"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."

Bryan P.

The price is AU$636

AU$636

includes taxes & fees

29 Oct - 30 Oct

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

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

A park with swings, a bench, and a view of a body of water.

A kitchen with a stove, sink, and dining area with chairs and a table.

A two-story house with a red roof, white siding, and red shutters.

13. 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 AU$718

AU$718

includes taxes & fees

21 Oct - 22 Oct

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

A beach with chairs and a pier in the background.

A hot tub with a white deck and railing, surrounded by trees and a house in the background.

A restaurant interior with tables, chairs, and a green dinosaur-shaped salt shaker.

An aerial view of a marina with boats docked, surrounded by residential buildings and lush greenery.

14. 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)

9.6/10

Exceptional

(19 reviews)

"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."

Sharon Z.

The price is AU$696

AU$696

includes taxes & fees

30 Sept - 1 Oct

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

A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

A dining area with a glass table, white chairs, a window with curtains, and a door.

A living room with a sofa, TV, and a patterned rug.

A compact kitchen with a sink, a window, and a built-in shelf with dishes.

15. Plum Point Cottage #17

Plum Point Cottage #17

Huntingtown

The price is AU$639

AU$639

includes taxes & fees

10 Oct - 11 Oct

Plum Point Cottage #17

A wooden interior with a dining area, sofas, and a table.

A wooden hallway with a staircase, a mirror, and a small table with a bowl and flowers.

A cozy living room with a leather sectional sofa, a fireplace, and a flat-screen TV mounted above it.

A wooden interior with a round dining table, white chairs, a hanging light fixture, and a window with a view of houses.

16. 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, (15 reviews)

9.0/10

Wonderful

(15 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."

Anonymous traveller

The price is AU$939

AU$939

includes taxes & fees

30 Sept - 1 Oct

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

A market with a covered seating area and a sign indicating parking for curbside pickup.

A dining area with a round table, four chairs, a chandelier, and a spiral staircase.

A room with a door leading outside, a ceiling fan, a bench, a radiator, and a window with a decorative panel.

A covered deck with two wicker chairs and a white door.

17. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage

North Beach

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."

Sharon t.

The price is AU$605

AU$605

includes taxes & fees

30 Sept - 1 Oct

Rose Haven Coastal Cottage

A deck with outdoor furniture, a red door, and a house with windows.

A living room with a sofa, ottoman, TV, and dining area with chairs and a table.

A bedroom with a bed, a nightstand, a lamp, a guitar, a window with curtains, and a ceiling fan.

A modern kitchen with wooden cabinets, stainless steel appliances, a round dining table with stools, and a ceiling fan.

18. 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

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"

David S.

The price is AU$531

AU$531

includes taxes & fees

26 Oct - 27 Oct

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

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

A calm lake with a wooden dock extending into the water, surrounded by trees and buildings in the background.

A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

A spacious living room with a fireplace, a round wooden dining table with chairs, a sofa, and a large window offering a view of a lake.

19. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!

Shady Side

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."

Michelle H.

The price is AU$815

AU$815

includes taxes & fees

6 Oct - 7 Oct

Sunset Cottage - West River Access and Views!

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

A sandy beach with a calm water body, wooden piers, and a distant shoreline with buildings and trees.

A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a large window.

A cozy living room with a large window overlooking a body of water, a leather sofa, a coffee table, and a patterned rug.

20. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home

Arundel on the Bay

9.8 out of 10, Exceptional, (78 reviews)

9.8/10

Exceptional

(78 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! "

Whitney M.

The price is AU$1,002

AU$1,002

includes taxes & fees

30 Sept - 1 Oct

Charming Annapolis WaterVIEW Home

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 Place Kent Narrows & Marina

8/10 Good

"The room was just ok nothing spectacular about the room/ decors The caulking around bathroom area looked like half was missing we had water view For a new hotel and the cost I would of expected better"

Carol 2-night trip

Posted 23 hours ago

Hyatt Place Kent Narrows & Marina

Holiday Inn Express Easton by IHG

8/10 Good

"Hotel was nice…My only complaint was you can hear whomever was outside of your door or near your room…Other than that the stay was good."

Deborah 1-night trip

Posted 2 days ago

Holiday Inn Express Easton by IHG

Comfort Inn & Suites Cambridge

8/10 Good

"Decent hotel for the price, clean. Wifi wasn't great."

Jennifer 2-night trip

Posted 2 days ago

Comfort Inn & Suites Cambridge

Hyatt Regency Chesapeake Bay

10/10 Excellent

"Beautiful location. Indoor pool is fabulous."

Carolyn 5-night trip

Posted 2 days ago

Hyatt Regency Chesapeake Bay

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Good stay. I wish I could have used the spa. It was closed on tuesdays. I also wish they could have provided free breakfast for the price that they charge per room"

Rathna 1-night trip

Posted 4 days ago

The Inn at Chesapeake Bay Beach Club

Baymont by Wyndham Easton

8/10 Good

"Staff was courteous and breakfast was adequate"

Ellen 1-night trip

Posted 4 days ago

Baymont by Wyndham Easton

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Pet friendly. Full breakfast. Desk was accommodating for a ground floor room for my dog. Room was clean and comfortable."

Wayne 1-night trip

Posted 6 days ago

Holiday Inn Express Annapolis East-Kent Island by IHG

Cambridge Inn

10/10 Excellent

"Good, clean room for a reasonable rate!"

Alexander 3-night trip

Posted 8 days ago

Cambridge Inn

Find out more about Royal Oak

Royal Oak Holiday Homes information

Number of reviews	386
Accommodation	351 Holiday Homes
Lowest Price	AU$354
Highest Price	AU$1,002

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Royal Oak on Expedia.com

Holiday Homes in Royal Oak

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Royal Oak holiday homes

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

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

3. More, than just a place to sleep - welcome home!

4. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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

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

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

8. Waterfront Getaway with Dock

9. Sunset Breezes - quiet waterfront retreat

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

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

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

13. 3-bedroom house in Deale located on Bay many amenities and great views

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

15. Plum Point Cottage #17

16. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

17. Rose Haven Coastal Cottage

18. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

19. Sunset Cottage - West River Access and Views!

20. Charming Annapolis WaterVIEW Home

Find holiday rentals that suit your style

Top Royal Oak Hotel Reviews

Hyatt Place Kent Narrows & Marina

Find out more about Royal Oak

Royal Oak Holiday Homes information

Explore a world of travel with Expedia

4. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8