Holiday Rentals Royal Oak from £205: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Royal Oak holiday rentals

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

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

Stevensville

Dawn G.

includes taxes & fees

23 Sept - 24 Sept

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

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

Cambridge

Robert

includes taxes & fees

28 Sept - 29 Sept

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

3. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

includes taxes & fees

28 Sept - 29 Sept

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

Downtown Cambridge

Kristen S.

includes taxes & fees

28 Sept - 29 Sept

A modern exterior with a black door, a metal staircase, and a lantern.

5. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with dark cabinets, a white countertop, and a large window.

6. Cass-N-Reel Luxury Houseboat

Grasonville

Danny B.

includes taxes & fees

8 Oct - 9 Oct

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

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

Cambridge

Jill C.

includes taxes & fees

23 Sept - 24 Sept

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

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

North Beach

Johanna S.

includes taxes & fees

28 Sept - 29 Sept

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Top Royal Oak Hotel Reviews

Comfort Inn & Suites Cambridge

10/10 Excellent

"The GM gave out goodie bags with handwritten notes to those who were participating in the Ironman race. The staff was very sweet. Good property for the price and located in decent proximity to the race."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Gorgeous hotel. I wish we had been there more than a night just to enjoy the various outdoor areas to relax. Enjoyed drinks and apps at their restaurants and had great coffee and breakfast at their market. We definitely want to go back when we have more time. We stayed in the Barn and it was just beautiful and quiet."

Wylder Tilghman Island

8/10 Good

"Property is well maintained and clean. The rooms are small but adequate. Our only fault was the restaurant pricing. Dishes are at least 25 to 40 percent upvharged. For example, a bowl of gazpacho was priced at $18 . If crab eas added it would have been $15 more for a grand total of $33 for a bowl of soup. Outrageous. I’ve been to 5 star restaurants and never paid that much for a bowl of soup. The chicken entree was $30 and the chicken consisted of 2 small chicken finger type pieces. No full breast or thigh/leg. Drinks definitely upcheged. Drive a bit down the road and eat at Chesapeake seafood or drive into town. If you don’t feel comfortable driving at night, go in and have a late lunch or get takeout."

Find out more about Royal Oak

Everything you need to know about Royal Oak holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Royal Oak holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Royal Oak holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Royal Oak holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Royal Oak holiday rentals we have selected for you start as low as £205 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Royal Oak rentals

At Expedia, we put the best Royal Oak holiday 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 holiday.

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 holiday rental in Royal Oak?

Yes, there are holiday rentals close to the most popular sights in Royal Oak, or you can select a more secluded option if you're looking for a relaxing stay. Royal Oak is known for its waterfront.

What are some of the best holiday rentals that Royal Oak has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Royal Oak is located near the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Royal Oak?

Expedia has 10 holiday 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 wider area, you’ll find Oxford Museum and Saint Michaels Village.

What are holiday rentals like in Royal Oak?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Royal Oak. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Royal Oak holiday rentals

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