Massey Holiday Rentals

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Holiday Rentals in Massey

Holiday Home in Dover

10.0 out of 10, Exceptional, (1)
"Host was great"
United States
mark o.
Charming 3-bedroom Ranch in delightful Dover with AC

Holiday Home in Perryville

10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Holiday Home in Elkton

10.0 out of 10, Exceptional, (178)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach

Cottage in Earleville

9.8 out of 10, Exceptional, (59)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Cottage in Elkton

9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is NZ$275
includes taxes & fees
8 Dec - 9 Dec
First Floor Studio Apartment in Historic Chestertown

Holiday Home in Perryville

9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is NZ$1,041
includes taxes & fees
10 Dec - 11 Dec
5-bedroom vacation home 5 minutes from historic Charlestown

Cabin in Elkton

9.6 out of 10, Exceptional, (14)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Mobile Home in Bear

Tiny Home Tranquil Oasis

Cabin in Chesapeake City

9.0 out of 10, Wonderful, (18)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is NZ$483
includes taxes & fees
11 Dec - 12 Dec
Historic Chesapeake City Stay

Holiday Home in Chesapeake City

10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Holiday Home in Perryville

10.0 out of 10, Exceptional, (279)
"Nothing more beautiful than staying by the water at Joe’s place!Such a wonderful place to unwind and refuel!"
United States
Doreen H.
Captivating Chesapeake experience

Holiday Home in Perryville

9.2 out of 10, Wonderful, (181)
"An amazing time and great family memories it simply was a delight and was very relaxing. So many things around to do. Definitely would stay again. "
United States
Stacey W.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Apartment in Elkton

9.8 out of 10, Exceptional, (40)
"Perfect in every way… a great stay"
United States
Robert B.
The price is NZ$193
includes taxes & fees
16 Dec - 17 Dec
Country Get Away 1 Bedroom Apartment

Villa in Earleville

9.8 out of 10, Exceptional, (20)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.

Holiday Home in Elkton

10.0 out of 10, Exceptional, (1)
"From start to finish this trip was AMAZING! Mr. Ray was accommodating and responded in a timely manner. The property was very well kept and had everything that was needed. Another thing that really stood out what that everything was labeled. We will definitely be booking another stay at The Pointe."
United States
Khadijah F.
The Pointe is on the Elk River on the Upper Chesapeake Bay

Holiday Home in North East

10.0 out of 10, Exceptional, (172)
"We had an amazing stay! The house has everything you could possibly need and is very clean. The location right on the water is glorious!"
United States
Natalie Q.
Nancy’s Touch, A Waterfront Paradise!

Apartment in Worton

10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is NZ$546
includes taxes & fees
7 Dec - 8 Dec
Waterfront Retreat with Private Dock and Beach

Mobile Home in Bear

10.0 out of 10, Exceptional, (4)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
Nature's Haven Tiny Home

Holiday Home in Chestertown

10.0 out of 10, Exceptional, (76)
"Great house, will stay again in the future. "
United States
Gary N.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
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 Massey Hotel Reviews

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, 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 NZ$193 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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Massey is located on a river, and has a patio, a garden 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 can relax into your holiday with a selection of games and 1 hot tub.

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 Betterton Beach. In the wider area, you’ll find Middletown Town Hall and Middletown Historic District.

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.