Massey Vacation Rentals

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Our top choices for Massey vacation rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $137
CA $219 total
includes taxes & fees
Jun 8 - Jun 9
First Floor Studio Apartment in Historic Chestertown

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is CA $149
CA $390 total
includes taxes & fees
Jun 14 - Jun 15
Historic Chesapeake City Stay

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (24 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is CA $94
CA $173 total
includes taxes & fees
Jun 3 - Jun 4
Guest Suite for up to 2 in a Victorian on the Chester River

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
The price is CA $97
CA $154 total
includes taxes & fees
Jun 8 - Jun 9
Country Get Away Studio Apartment

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

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is CA $131
CA $220 total
includes taxes & fees
Jun 14 - Jun 15
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (5 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is CA $221
CA $353 total
includes taxes & fees
Jun 8 - Jun 9
Mini Aruba RV/Glamping Tent

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is CA $261
CA $326 total
includes taxes & fees
Jun 4 - Jun 5
Nature's Haven Tiny Home

Right in the center of everywhere in Dover

Right in the center of everywhere in Dover
Dover
8.8 out of 10, Excellent, (5 reviews)
"Destination wedding location. Family, fun, and fellowship in this comfortable home with all the amenities! We played pool, enjoyed the central location, and used all the beds. Check in was easy and host was supportive. It met our needs and we felt right at home. "
United States
Linda K.
The price is CA $309
CA $657 total
includes taxes & fees
Jun 2 - Jun 3
Right in the center of everywhere in Dover

Beachcomber Suite

Beachcomber Suite
Kent County
The price is CA $201
CA $248 total
includes taxes & fees
Jun 8 - Jun 9
Beachcomber Suite

Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (7 reviews)
"Place was super nice, and beautiful. Owners very responsive. My only thing was not coffee maker so if you are a coffee drinker bring coffee pot lol. Other then that place it absolutely beautiful "
United States
vincent
The price is CA $348
CA $492 total
includes taxes & fees
Jun 2 - Jun 3
Elegant Family Stay • Quiet Neighborhood • Comfort

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
The price is CA $261
CA $333 total
includes taxes & fees
Jun 2 - Jun 3
Tiny Home Tranquil Oasis

Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $238
CA $293 total
includes taxes & fees
Jun 4 - Jun 5
Turtle Cove Room

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is CA $345
CA $531 total
includes taxes & fees
Jun 3 - Jun 4
Newly restored apartment in the heart of Chestertown

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (153 reviews)
"This is the second time my group of friends has stayed here. The house is very comfortable and well-appointed, and the view is gorgeous! "
United States
Melinda S.
The price is CA $394
CA $774 total
includes taxes & fees
Jun 2 - Jun 3
5-bedroom vacation home 5 minutes from historic Charlestown

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is CA $310
CA $522 total
includes taxes & fees
Jun 15 - Jun 16
Waterfront Retreat with Private Dock and Beach

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is CA $599
CA $884 total
includes taxes & fees
Jun 23 - Jun 24
Long Beach Cottage, (romantic couple’s getaway)

Sunset River Cottage

Sunset River Cottage
Elkton
8.6 out of 10, Excellent, (16 reviews)
"The property was just what we needed. Very quiet, laid back and the pier was great for fishing!"
United States
Ray D.
Sunset River Cottage

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
9.0 out of 10, Wonderful, (4 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is CA $568
CA $675 total
includes taxes & fees
Jun 4 - Jun 5
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Top Floor Master Suite Bay View

Top Floor Master Suite Bay View
3.0 star property
North East
The price is CA $611
CA $823 total
includes taxes & fees
Jun 26 - Jun 27
Top Floor Master Suite Bay View
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Massey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Earleville Wildlife Management Area. In the larger area, you’ll find Crow Farm and Vineyard and Cecilton Branch Cecil County Public Library.

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.