Massey Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Massey holiday rentals

Property grounds

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 HK$776
HK$1,245 total
includes taxes & fees
1 Jun - 2 Jun
First Floor Studio Apartment in Historic Chestertown
Marina

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 HK$846
HK$2,201 total
includes taxes & fees
11 Jun - 12 Jun
Historic Chesapeake City Stay
Exterior

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, (23 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 HK$533
HK$980 total
includes taxes & fees
1 Jun - 2 Jun
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

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 HK$549
HK$872 total
includes taxes & fees
8 Jun - 9 Jun
Country Get Away Studio Apartment
Interior

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 HK$768
HK$1,273 total
includes taxes & fees
23 Jun - 24 Jun
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Pool

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 HK$1,254
HK$1,984 total
includes taxes & fees
8 Jun - 9 Jun
Mini Aruba RV/Glamping Tent
Terrace/patio

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 HK$1,481
HK$1,814 total
includes taxes & fees
1 Jun - 2 Jun
Nature's Haven Tiny Home
Fridge, microwave, oven, dishwasher

Right in the center of everywhere in Dover

Right in the center of everywhere in Dover
Dover
8.6 out of 10, Excellent, (4 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 HK$1,756
HK$3,747 total
includes taxes & fees
1 Jun - 2 Jun
Right in the center of everywhere in Dover
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
The price is HK$1,143
HK$1,412 total
includes taxes & fees
1 Jun - 2 Jun
Beachcomber Suite
Exterior

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 HK$1,975
HK$2,761 total
includes taxes & fees
1 Jun - 2 Jun
Elegant Family Stay • Quiet Neighborhood • Comfort
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
The price is HK$1,481
HK$1,853 total
includes taxes & fees
1 Jun - 2 Jun
Tiny Home Tranquil Oasis
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is HK$1,354
HK$1,675 total
includes taxes & fees
4 Jun - 5 Jun
Turtle Cove Room
Smart TV, books

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 HK$1,959
HK$3,002 total
includes taxes & fees
3 Jun - 4 Jun
Newly restored apartment in the heart of Chestertown
Sun-loungers, beach towels

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 HK$2,236
HK$4,372 total
includes taxes & fees
2 Jun - 3 Jun
5-bedroom vacation home 5 minutes from historic Charlestown
Beach

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 HK$1,763
HK$2,967 total
includes taxes & fees
15 Jun - 16 Jun
Waterfront Retreat with Private Dock and Beach
TV, fireplace

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 HK$3,406
HK$5,025 total
includes taxes & fees
23 Jun - 24 Jun
Long Beach Cottage, (romantic couple’s getaway)
Dining

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
Interior

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 HK$3,225
HK$3,834 total
includes taxes & fees
4 Jun - 5 Jun
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Outdoor pool

Top Floor Master Suite Bay View

Top Floor Master Suite Bay View
3.0 star property
North East
The price is HK$3,473
HK$4,678 total
includes taxes & fees
11 Jun - 12 Jun
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"We were given a suite"
Donna 1-night trip
Posted less than an hour ago
Bally's Dover Casino Resort

Find out more about Massey

Search for holiday rentals in Massey on Expedia! You can easily find your home rentals, villas, holiday apartments in Massey using one of the methods below:

  • View our selection of featured holiday rentals in Massey
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  • Enter your travel dates to view the best deals on holiday rentals in Massey while they last

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

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?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Massey is located on a lake, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Make the most of Access to 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 wider area, you’ll find Crow Farm and Vineyard and Cecilton Branch Cecil County Public Library.

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.