Massey Vacation Rentals from $159: Search Short-Term Rentals

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

Sailor's Sunrise Cottage - Chesapeake Bay : Visitors like this Massey vacation home rental. It is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

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In two weeks

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Our top choices for Massey vacation rentals

Historic Chesapeake City Stay

Chesapeake City

Manjetjola P.

$260 nightly

Jun 22 - Jun 23

Total with taxes and fees

Country Get Away Studio Apartment

Elkton

Robert B.

$105 nightly

Jul 2 - Jul 3

Total with taxes and fees

Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

$118 nightly

Jun 29 - Jun 30

Total with taxes and fees

First Floor Studio Apartment in Historic Chestertown

Chestertown

lesia k.

$144 nightly

Jun 22 - Jun 23

Total with taxes and fees

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Dover

Richard B.

$153 nightly

Jun 30 - Jul 1

Total with taxes and fees

Mini Aruba RV/Glamping Tent

Dover

Marleen M.

$237 nightly

Jun 30 - Jul 1

Total with taxes and fees

Tiny Home Tranquil Oasis

Bear

Megan M.

$228 nightly

Jun 22 - Jun 23

Total with taxes and fees

Turtle Cove Room

Kent County

$160 nightly

Jul 6 - Jul 7

Total with taxes and fees

Nature's Haven Tiny Home

Bear

Maxwell

$223 nightly

Jun 22 - Jun 23

Total with taxes and fees

Beachcomber Suite

Kent County

$166 nightly

Jun 22 - Jun 23

Total with taxes and fees

Right in the center of everywhere in Dover

Dover

Linda K.

$469 nightly

Jul 1 - Jul 2

Total with taxes and fees

Waterfront Retreat with Private Dock and Beach

Worton

Jennifer W.

$343 nightly

Jun 28 - Jun 29

Total with taxes and fees

Long Beach Cottage, (romantic couple’s getaway)

Charlestown

Mike F.

$617 nightly

Jul 1 - Jul 2

Total with taxes and fees

Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

$349 nightly

Jun 22 - Jun 23

Total with taxes and fees

Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle

vincent

$357 nightly

Jul 21 - Jul 22

Total with taxes and fees

Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones

Middletown

$746 nightly

Jul 7 - Jul 8

Total with taxes and fees

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Top Massey Hotel Reviews

Red Roof Inn & Suites Dover Downtown

8/10 Good

"No comments."

Comfort Suites Dover University Area

8/10 Good

"I stayed for 2 nights. The hotel is located within a 2 minute walk of both Wendy's and Bob Evans restaurants, and near shopping. The room was spacious, the bathroom had been updated, and the air conditioner worked perfectly. The pool was very nice - the water was clear, cool, and very refreshing. The pool deck area was amply sized, with louners and a table with an umbrella. 2 negatives: 1) The breakfast was okay, but could be more extravagant, to offer more protein choices. There was no peanut butter to put on toast, which I see as a staple of most hotels. 2) The door to my room was not sealed tightly and allowed a lot of light into the room at night. When I mentioned this to the staff, they brought up strip insulation and did the best they could do to address this problem, so I give them high marks for that! Overall, a nice place to stay on a budget."

MHO Hotel Dover

8/10 Good

"The hotel should have been totally renovated by professionals after being purchased from Super 8. Super 8 items are still being used . Sidewalks and parking lots are not clean. Grass needed mowing Dning room is not clean, including table floors and chairs. Lots of young local residents liv there permanently and walk about the premises at all times."

Find out more about Massey

Everything you need to know about Massey vacation rentals

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

Massey vacation 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 low season months. For more hustle and bustle, you may prefer to visit Massey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Massey rentals

At Expedia, we put the best Massey vacation 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 vacation.

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.

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Frequently asked questions

Can I find vacation rentals in Massey?

Yes, we have vacation rentals close to well known attractions in Massey, or you can choose a secluded option if you're looking for relaxation.

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

Sailor's Sunrise Cottage - Chesapeake Bay: Visitors like this Massey vacation home rental. It is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

What’s there to see and do in Massey?

Explore the area and family-friendly sights such as Frightland, or get out into nature at a spot like Betterton Beach. In the larger area, you’ll find Middletown Town Hall and Middletown Historic District.

What’s a vacation rental in Massey like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Massey. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for family gatherings.

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Check prices for these dates

Our top choices for Massey vacation rentals

Historic Chesapeake City Stay

Country Get Away Studio Apartment

Guest Suite for up to 2 in a Victorian on the Chester River

First Floor Studio Apartment in Historic Chestertown

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Mini Aruba RV/Glamping Tent

Tiny Home Tranquil Oasis

Turtle Cove Room

Nature's Haven Tiny Home

Beachcomber Suite

Right in the center of everywhere in Dover

Waterfront Retreat with Private Dock and Beach

Long Beach Cottage, (romantic couple’s getaway)

Newly restored apartment in the heart of Chestertown

Elegant Family Stay • Quiet Neighborhood • Comfort

Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones

Find vacation rentals that suit your style

Top Massey Hotel Reviews

Red Roof Inn & Suites Dover Downtown

Bally's Dover Casino Resort

Sleep Inn & Suites Dover University Area

Quality Inn Smyrna

Comfort Inn & Suites Dover near Speedway

Wyndham Garden Dover

Holiday Inn Express Hotel & Suites Dover by IHG

Comfort Suites Dover University Area

MHO Hotel Dover

Find out more about Massey

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