Massey Holiday Rentals from €151: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Massey has to offer?

Chesapeake Bay House with Dock & Private Beach : This holiday home rental outside of Massey is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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Holiday Rentals in Massey

Relax on the lakeside deck with a round table and four Adirondack chairs, surrounded by a rocky shoreline and a wooden pier.

"Great place for a long weekend. Easy travel to surrounding areas to explore."

Guests can enjoy a serene lakeside experience from this picturesque pier, featuring a table and chair for a peaceful retreat.

includes taxes & fees

3 Aug - 4 Aug

Stroll through the serene garden, featuring a picturesque arborway, vibrant flowers, and a birdhouse, surrounded by a tranquil body of water.

"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."

Relax in a serene hot tub surrounded by lush greenery and a tranquil view.

"We had a wonderful stay! Really enjoyed the eagles and osprey. The hot tub was amazing and the fire pit was nice to enjoy in the cold weather. All amenities were there that we needed, the location is great and the town is really cute. We will be back! "

Relax in this stylish living room with a large sofa, armchair, and ottoman, perfect for unwinding in comfort.

"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."

Relax by the pool surrounded by a tranquil golf course view.

"Very pretty location. Few minutes drive to town center."

includes taxes & fees

4 Aug - 5 Aug

Escape to a serene cabin surrounded by lush greenery and natural beauty.

Enjoy a serene beach experience with access to the ocean via the public pier.

"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."

Enjoy meals at the central island with a round table and two chairs in this well-equipped kitchen.

"Property is beautiful, host answered our questions in a timely manner. Would stay again "

Enjoy waterfront views from the dock and outdoor seating area, situated near a scenic bridge and lush green surroundings.

"Always a nice get away…."

includes taxes & fees

25 Jul - 26 Jul

Enjoy al fresco dining and relaxation on this serene outdoor deck with a barbecue grill and comfortable seating.

"Enjoyed"

includes taxes & fees

22 Jul - 23 Jul

Guests can enjoy a serene lake view from the pier, surrounded by lush greenery.

"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"

includes taxes & fees

23 Jul - 24 Jul

Relax in this inviting living space with a comfortable sofa, a cozy bed, and a peaceful atmosphere.

"Located in a quite area and the host were incredible"

Relax on the pier with a view of distant landforms.

"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "

Simple, two-story building with a flat roof, surrounded by trees in a tranquil setting.

"The house is roomy and was clean and well stocked."

Enjoy cooking in this well-equipped kitchen with a central island and bench, featuring stainless steel appliances and ample cabinetry.

"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."

Stroll through the serene garden, surrounded by lush plants and a majestic tree.

"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "

Enjoy a scenic view of the lake from this kitchen, featuring a large window and stainless steel appliances.

"This is a gorgeous property with a great water view of the canalThe house is beautifully decorated and comfortable, and we loved the upper deck. We had a few issues and Gwen addressed them quickly. The restaurants in town are great and in walking distance. There are interesting areas nearby to explore. "

Stroll through the serene garden, surrounded by vibrant flowers and a charming birdcage.

"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."

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Top Massey Hotel Reviews

Bally's Dover Casino Resort

10/10 Excellent

"Clean and spacious room. "

Find out more about Massey

Everything you need to know about Massey 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 Massey 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 Massey holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Massey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Massey. 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 Massey 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 Massey holiday rentals we have selected for you start as low as €151 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Massey rentals

At Expedia, we put the best Massey 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 Massey 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 Massey 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 Massey. 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 holiday rentals in Massey?

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

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

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Massey is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Massey?

Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Earleville Wildlife Management Area. In the wider area, you’ll find Tilmon's Island Winery and Westown.

What’s a holiday rental in Massey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Massey. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for small groups.

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Holiday Rentals in Massey

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Holiday Rentals in Massey

Chesapeake Bay House with Dock & Private Beach

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Charming 2-bedroom cabin close to Fair Hill on horse farm

Nancy’s Touch, A Waterfront Paradise!

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

First Floor Studio Apartment in Historic Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Historic Chesapeake City Stay

Nature's Haven Tiny Home

Waterfront Retreat with Private Dock and Beach

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

Captivating Chesapeake experience

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Historic Downtown Garden Oasis with Private Patio

Luxury 2-bedroom house with Water views, Chesapeake City

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Top Massey Hotel Reviews

Bally's Dover Casino Resort

Comfort Inn & Suites Chestertown

Fairfield Inn & Suites by Marriott Dover

Holiday Inn Express Hotel & Suites Dover by IHG

Sleep Inn And Suites

Hampton Inn Dover

Hampton Inn Middletown

Days Inn by Wyndham Dover Downtown

Fairfield Inn & Suites by Marriott Middletown

Find out more about Massey

Frequently asked questions