Massey Holiday Rentals

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Holiday Rentals in Massey

Apartment in Elkton

9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is AU$171
includes taxes & fees
15 Dec - 16 Dec
Country Get Away 1 Bedroom Apartment

Apartment in Millington

9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$191
includes taxes & fees
9 Dec - 10 Dec
Guest Suite for up to 2 in a Victorian on the Chester River

Cabin in Chesapeake City

9.0 out of 10, Wonderful, (19)
"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 AU$424
includes taxes & fees
9 Dec - 10 Dec
Historic Chesapeake City Stay

Apartment in Chestertown

9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is AU$242
includes taxes & fees
9 Dec - 10 Dec
First Floor Studio Apartment in Historic Chestertown

Holiday Home in Smyrna

9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AU$544
includes taxes & fees
10 Dec - 11 Dec
Amazing Modern house with a full kitchen and parking

Holiday Home in Elkton

8.0 out of 10, Very good, (10)
"Nice and quiet place to stay"
United States
Gary M.
The price is AU$428
includes taxes & fees
9 Dec - 10 Dec
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Apartment in Chesapeake City

2.0 star property
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is AU$510
includes taxes & fees
9 Dec - 10 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cottage in Charlestown

10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is AU$591
includes taxes & fees
9 Dec - 10 Dec
Long Beach Cottage, (romantic couple’s getaway)

Cottage in Betterton

The price is AU$634
includes taxes & fees
1 Jan - 2 Jan 2026
Grandma’s Cottage will wrap around you like a warm hug

Holiday Home in Kent County

The price is AU$307
includes taxes & fees
9 Dec - 10 Dec
High Tide Haven Suite

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 AU$474
includes taxes & fees
9 Dec - 10 Dec
Waterfront Retreat with Private Dock and Beach

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 AU$915
includes taxes & fees
10 Dec - 11 Dec
5-bedroom vacation home 5 minutes from historic Charlestown

Holiday Home in Middletown

2.0 star property
The price is AU$750
includes taxes & fees
15 Dec - 16 Dec
Heated Pool • Private Backyard • Home Theater

Holiday Home in Smyrna

10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is AU$898
includes taxes & fees
15 Dec - 16 Dec
JVA LUXURY HOUSING
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$171 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?

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.