Massey Vacation Rentals

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Check prices for these dates

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Massey

Property grounds
Country Get Away 1 Bedroom Apartment

Apartment in Elkton

9.8 out of 10, Exceptional, (40)
"Perfect in every way… a great stay"
United States
Robert B.
The price is ￥10,856
￥17,261 total
includes taxes & fees
Dec 11 - Dec 12
Country Get Away 1 Bedroom Apartment
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

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 ￥10,545
￥19,397 total
includes taxes & fees
Dec 10 - Dec 11
Guest Suite for up to 2 in a Victorian on the Chester River
Marina
Historic Chesapeake City Stay

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 ￥16,749
￥43,234 total
includes taxes & fees
Dec 7 - Dec 8
Historic Chesapeake City Stay
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,353
￥24,633 total
includes taxes & fees
Dec 9 - Dec 10
First Floor Studio Apartment in Historic Chestertown
Dining
Amazing Modern house with a full kitchen and parking

Vacation 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 ￥27,914
￥55,379 total
includes taxes & fees
Dec 10 - Dec 11
Amazing Modern house with a full kitchen and parking
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Vacation Home in Elkton

8.0 out of 10, Very Good, (10)
"Nice and quiet place to stay"
United States
Gary M.
The price is ￥20,936
￥43,562 total
includes taxes & fees
Dec 7 - Dec 8
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

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 ￥27,914
￥51,945 total
includes taxes & fees
Dec 10 - Dec 11
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Outdoor spa tub
Long Beach Cottage, (romantic couple’s getaway)

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 ￥35,678
￥60,238 total
includes taxes & fees
Dec 7 - Dec 8
Long Beach Cottage, (romantic couple’s getaway)
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

The price is ￥34,893
￥64,603 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
High Tide Haven Suite

Vacation Home in Kent County

The price is ￥26,868
￥30,962 total
includes taxes & fees
Dec 7 - Dec 8
High Tide Haven Suite
Beach
Waterfront Retreat with Private Dock and Beach

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 ￥27,139
￥48,295 total
includes taxes & fees
Dec 8 - Dec 9
Waterfront Retreat with Private Dock and Beach
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

Vacation 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 ￥50,106
￥93,223 total
includes taxes & fees
Dec 10 - Dec 11
5-bedroom vacation home 5 minutes from historic Charlestown
A heated pool
Heated Pool • Private Backyard • Home Theater

Vacation Home in Middletown

2.0 star property
The price is ￥24,503
￥78,252 total
includes taxes & fees
Dec 15 - Dec 16
Heated Pool • Private Backyard • Home Theater
Private kitchen
JVA LUXURY HOUSING

Vacation 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 ￥62,032
￥91,342 total
includes taxes & fees
Dec 11 - Dec 12
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

Fairfield Inn & Suites by Marriott Dover

Fairfield Inn & Suites by Marriott Dover

10/10 Excellent
"Clean room, quiet environment, great breakfast options and professional staff. "
Lisa 2-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Dover

Find out more about Massey

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Look no further and take a look at our great range of rental properties in Massey!

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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: Visitors like this Massey vacation home rental. It is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a 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 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.