Royal Oak Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Royal Oak vacation rentals

A living room with two grey sofas, a coffee table, and a ceiling fan.

1. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

$291 nightly

Nov 8 - Nov 9

Total with taxes and fees

2. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

$272 nightly

Nov 8 - Nov 9

Total with taxes and fees

3. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

Easton

Lynn G.

$379 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

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

Cambridge

Jill C.

$472 nightly

Nov 8 - Nov 9

Total with taxes and fees

A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

5. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

$233 nightly

Nov 7 - Nov 8

Total with taxes and fees

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

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

Cambridge

Mary Beth S.

$359 nightly

Nov 30 - Dec 1

Total with taxes and fees

A marina with boats docked, a water tower, and residential buildings with balconies.

7. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Cambridge

mike

$448 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

8. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

$228 nightly

Nov 8 - Nov 9

Total with taxes and fees

9. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

$356 nightly

Dec 1 - Dec 2

Total with taxes and fees

A deck with a view of a marina, including boats and docks.

10. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

$233 nightly

Nov 12 - Nov 13

Total with taxes and fees

A dining area with a round table, chairs, and a decorative table runner.

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

Cambridge

$345 nightly

Nov 7 - Nov 8

Total with taxes and fees

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

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

North Beach

Johanna S.

$276 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

13. Relax on Kent Island in 4 Bedroom Home w/Waterview

Stevensville

Anthony P.

$315 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

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

Stevensville

Michael V.

$276 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

15. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

$294 nightly

Nov 9 - Nov 10

Total with taxes and fees

A house with a yellow door and a window with a lamp outside.

16. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

$281 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

North Beach

Sarah

$423 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

18. Waterfront Getaway with Dock

Woolford

Mills Family A.

$239 nightly

Nov 8 - Nov 9

Total with taxes and fees

19. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Ben W.

$369 nightly

Dec 2 - Dec 3

Total with taxes and fees

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

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

Cambridge

Anonymous traveler

$451 nightly

Nov 11 - Nov 12

Total with taxes and fees

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Find vacation rentals that suit your style

Top Royal Oak Hotel Reviews

A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

St Michaels Inn

St. Michaels

10/10 Excellent

Lori

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

Sandaway Suites & Beach

Oxford

10/10 Excellent

joseph

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

The Oaks Waterfront

Easton

10/10 Excellent

William

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

A modern hotel dining area with a long table, four chairs, and three pendant lights.

Hampton Inn Easton

Easton

10/10 Excellent

Anonymous traveler

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

The Tidewater Inn

Easton

10/10 Excellent

Maria

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

A waterfront property with a covered patio, a dock, and a boat.

Wylder Tilghman Island

Tilghman

10/10 Excellent

We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer. The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain. The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day. We look...

Alan

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...

Nancy

An indoor swimming pool with lounge chairs and a no diving sign.

Holiday Inn Express Easton by IHG

Easton

10/10 Excellent

Belinda

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

George Brooks House B&B

St. Michaels

10/10 Excellent

Excellent B&B with a pool! the pool was clutch because we were there probably on the hottest days of the year so going in after a long day of walking around was nice. Used the pool until 10pm. Food was good, room was clean, people were nice. What else could you ask for. The only thing I noticed (and it wasn't a big deal) was the mirror in the room was too low on the wall (I'm 5'8 and still had to bend a little) and there was only one mirror so if you're in a hurry getting ready with your spouse...

Anonymous traveler

A large, two-story house with a prominent tower and a covered porch.

Hummingbird Inn

Easton

10/10 Excellent

My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...

Robert

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

Baymont by Wyndham Easton

Easton

10/10 Excellent

Hannah

A resort with a large pool, outdoor seating, and a view of the sea.

Hyatt Regency Chesapeake Bay

Cambridge

10/10 Excellent

Sue

A sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.

Marvel's on the Creek

East New Market

10/10 Excellent

This was my first time @ a bed and breakfast. The owners, Debbie and Allen are amazing. Being an introvert and there for an Ironman race, I was concerned about having to interact too much with other people. Debbie struck the perfect balance of being available but also giving people space to hide away. The property is gorgeous and clean. Her breakfasts are amazing (eggs cooked to order, bacon, biscuits, quiche, homefries, etc). She goes above and beyond to make people feel welcomed. She woke up...

Joseph

A breakfast buffet with various food items and a sign indicating complimentary breakfast hours.

Holiday Inn Express Cambridge by IHG

Cambridge

10/10 Excellent

Charles A

Two Adirondack chairs facing a calm body of water with a clear sky above.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

Find out more about Royal Oak

Everything you need to know about Royal Oak vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Royal Oak vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Royal Oak vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Royal Oak vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Royal Oak. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Royal Oak in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $241 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Royal Oak rentals

At Expedia, we put the best Royal Oak vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Royal Oak rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Royal Oak vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Royal Oak. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Royal Oak?

Yes, you can find vacation rentals near popular attractions in Royal Oak, or you can select a more remote option if you're looking for a relaxing stay. Royal Oak is known for its waterfront.

What's the top vacation rental in Royal Oak?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Royal Oak vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Royal Oak?

Expedia has 11 vacation rentals for your stay in Royal Oak.

What can I see and do in Royal Oak?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Gerry Boyle Park at Great Marsh. In the larger area, you’ll find Oxford Museum and Saint Michaels Village.

What are vacation rentals like in Royal Oak?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Royal Oak. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.

Royal Oak Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Royal Oak vacation rentals

1. Cambridge Apt in Walkable Neighborhood

2. Cambridge Apt in Walkable Neighborhood

3. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

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

5. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

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

7. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

8. Sailwinds Loft at Cambridge Creek

9. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

10. Cass-N-Reel Luxury Houseboat

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

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

13. Relax on Kent Island in 4 Bedroom Home w/Waterview

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

15. The Cozy Crab- Your Charming Haven in Lovely North Beach!

16. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

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

18. Waterfront Getaway with Dock

19. Family Beach House: Spacious Deck, Grill & Views

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

Find vacation rentals that suit your style

Top Royal Oak Hotel Reviews

Knapps Narrows Marina & Inn

10/10 Excellent

Find out more about Royal Oak

Everything you need to know about Royal Oak vacation rentals

Royal Oak vacation rentals: An excellent choice for every season

How to find incredible deals on Royal Oak rentals

Frequently Asked Questions

Can I find a vacation rental in Royal Oak?

What's the top vacation rental in Royal Oak?

How many vacation rentals are there in Royal Oak?

What can I see and do in Royal Oak?

What are vacation rentals like in Royal Oak?

Explore a world of travel with Expedia

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