Massey Holiday Rentals

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Holiday Rentals in Massey

Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (174)
"Nice property. Large enough for 13. Plenty of space to spread out "
United States
Mike J.
Chesapeake Bay House with Dock & Private Beach
Charming 3-bedroom Ranch in delightful Dover with AC
Charming 3-bedroom Ranch in delightful Dover with AC
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (101)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
United States
Skye M.
Waterfront house with amazing views. Top of the Chesapeake
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
9.8 out of 10, Exceptional, (12)
"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
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
United States
Michael S.
The price is AU$433
includes taxes & fees
26 Oct - 27 Oct
Historic Chesapeake City Stay
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
10.0 out of 10, Exceptional, (10)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (58)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Charming 2-bedroom cabin close to Fair Hill on horse farm
9.6 out of 10, Exceptional, (8)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (146)
" The location and the house! Great communication from owner!! Thank you!!"
United States
steve j.
The price is AU$933
includes taxes & fees
27 Oct - 28 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AU$483
includes taxes & fees
26 Oct - 27 Oct
Waterfront Retreat with Private Dock and Beach
Tiny Home Tranquil Oasis
The price is AU$375
includes taxes & fees
26 Oct - 27 Oct
Tiny Home Tranquil Oasis
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (105)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AU$247
includes taxes & fees
27 Oct - 28 Oct
First Floor Studio Apartment in Historic Chestertown
Stunning waterfront villa with indoor pool and kids swing set and play area.
9.8 out of 10, Exceptional, (19)
"This was the perfect house for the occasion, the rooms were spacious and there was a lot of spaces to gather. We didn’t leave for the whole weekend and it was amazing. The property is beautiful and the lake is serene. Thanks for letting us stay! Would love to come back. "
United States
Kelly & Devin V.
Stunning waterfront villa with indoor pool and kids swing set and play area.
High Tide Haven Suite
The price is AU$317
includes taxes & fees
25 Oct - 26 Oct
High Tide Haven Suite
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.8 out of 10, Exceptional, (51)
"Perfect getaway weekend with beautiful sunset views. Condo is very well equipped and super clean. All the comforts of home! Definitely will stay there again! Thank you for sharing your home with us. "
United States
Linds B.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Sailor's Sunrise Cottage - Chesapeake Bay
9.4 out of 10, Exceptional, (53)
"Sweet cottage - the porch bedroom is the favorite!"
United States
Katherine D.
Sailor's Sunrise Cottage - Chesapeake Bay
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
9.8 out of 10, Exceptional, (18)
"We all got together from various parts of the country to enjoy ourselves at this lovely place."
United States
MARK M.
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Eastern shore beachfront cottage with stunning sunset views!
10.0 out of 10, Exceptional, (3)
"This property is stunning, from the views, to the accommodations and furnishing. Great location, easy access to town and amenities. The host is responsive, and incredibly kind. Highly recommend!!"
United States
Jessica J.
Eastern shore beachfront cottage with stunning sunset views!
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
9.8 out of 10, Exceptional, (94)
"The properly is in great shape, clean and well provisioned. The flat back yard is perfect for yard games and when the tide is low, there a little private beach! The kids played in the sand and floated around Still Pound Creek all weekend. Loretta was an excellent host!"
United States
Adam H.
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (56)
"Amazing weekend on the river with a fantastic house. "
United States
Kendall S.
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
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 favourite 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 depend 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 AU$247 per night. Entering your travel dates in the search wizard might find you 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 Betterton Beach. In the wider area, you’ll find Tilmon's Island Winery and Hack's Point Marina.

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.