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Massey Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Massey vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (22 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is ￥17,420
￥44,454 total
includes taxes & fees
Jun 22 - Jun 23
Historic Chesapeake City Stay
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is ￥11,291
￥17,953 total
includes taxes & fees
Jul 2 - Jul 3
Country Get Away Studio Apartment
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
9.8 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 ￥10,968
￥20,175 total
includes taxes & fees
Jun 29 - Jun 30
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
"Every thing was great"
United States
lesia k.
The price is ￥15,969
￥25,621 total
includes taxes & fees
Jun 22 - Jun 23
First Floor Studio Apartment in Historic Chestertown
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, (4 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is ￥16,614
￥27,040 total
includes taxes & fees
Jun 30 - Jul 1
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, (6 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 ￥26,937
￥42,506 total
includes taxes & fees
Jun 30 - Jul 1
Mini Aruba RV/Glamping Tent
Terrace/patio

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 ￥30,486
￥38,149 total
includes taxes & fees
Jun 22 - Jun 23
Tiny Home Tranquil Oasis
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥22,647
￥28,104 total
includes taxes & fees
Jul 6 - Jul 7
Turtle Cove Room
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 ￥30,486
￥37,343 total
includes taxes & fees
Jun 22 - Jun 23
Nature's Haven Tiny Home
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
The price is ￥23,518
￥29,054 total
includes taxes & fees
Jun 22 - Jun 23
Beachcomber Suite
Fridge, microwave, oven, dishwasher

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 ￥36,293
￥77,284 total
includes taxes & fees
Jul 2 - Jul 3
Right in the center of everywhere in Dover
Beach nearby

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 ￥36,293
￥61,065 total
includes taxes & fees
Jun 28 - Jun 29
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 ￥82,924
￥119,076 total
includes taxes & fees
Jul 13 - Jul 14
Long Beach Cottage, (romantic couple’s getaway)
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, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥40,325
￥62,131 total
includes taxes & fees
Jun 22 - Jun 23
Newly restored apartment in the heart of Chestertown
Exterior

Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (9 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 ￥43,406
￥60,522 total
includes taxes & fees
Jun 26 - Jun 27
Elegant Family Stay • Quiet Neighborhood • Comfort
Outdoor dining

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

Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones
Middletown
The price is ￥101,425
￥112,071 total
includes taxes & fees
Jun 24 - Jun 25
Spacious Family Home | Seats 16, Sleeps 9 | 3 Sleeping/Privacy Zones
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

Comfort Suites Dover University Area

Comfort Suites Dover University Area

10/10 Excellent
"Clean room was very. I will book a stay again in the future."
Vanessa 2-night trip
Posted less than an hour ago
Comfort Suites Dover University Area

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:

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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?

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.