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Massey Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Massey vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (25 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
$263 nightly
The price is $279
Jul 20 - Jul 21
Total with taxes and fees
Historic Chesapeake City Stay
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
$105 nightly
The price is $111
Jul 23 - Jul 24
Total with taxes and fees
Country Get Away Studio Apartment
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"We had a lovely stay at Elisabeths place. She helped us with anything we needed. The aprtment was clean, cozy and just right for 2 people."
United States
Lisa v.
$144 nightly
The price is $159
Jul 21 - Jul 22
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
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.
$118 nightly
The price is $125
Jul 20 - Jul 21
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

Cozy Room in Dover

Cozy Room in Dover
Dover
$94 nightly
The price is $96
Jul 21 - Jul 22
Total with taxes and fees
Cozy Room in Dover
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
9.8 out of 10, Exceptional, (8 reviews)
"Woodland Hideaway was just that! A nice place to hideaway after hot and busy days. The place was clean, kitchen well stocked and the whole unit was quiet. It was located in a nice subdivision with lots of trees and beautiful flowers. It was the first trip my husband and I took our dog and it was a great place for the dog, quiet with lots of places for his daily walks. Thank you Kara!"
United States
Melanie
$169 nightly
The price is $174
Jul 28 - Jul 29
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
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
$226 nightly
The price is $235
Aug 3 - Aug 4
Total with taxes and fees
Nature's Haven Tiny Home
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.
$283 nightly
The price is $292
Jul 27 - Jul 28
Total with taxes and fees
Mini Aruba RV/Glamping Tent
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.
$343 nightly
The price is $379
Jul 19 - Jul 20
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
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.
$233 nightly
The price is $242
Jul 17 - Jul 18
Total with taxes and fees
Tiny Home Tranquil Oasis
Interior

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
$286 nightly
The price is $297
Jul 19 - Jul 20
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$172 nightly
The price is $187
Jul 27 - Jul 28
Total with taxes and fees
Beachcomber Suite
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
$160 nightly
The price is $174
Jul 27 - Jul 28
Total with taxes and fees
Turtle Cove Room
Fridge, microwave, oven, dishwasher

Right in the center of everywhere in Dover

Right in the center of everywhere in Dover
Dover
9.2 out of 10, Wonderful, (7 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.
Right in the center of everywhere in Dover
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 very clean and the host was EXCELLENT with fast communication "
United States
Chris R.
$386 nightly
The price is $399
Aug 10 - Aug 11
Total with taxes and fees
Elegant Family Stay • Quiet Neighborhood • Comfort
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.
$687 nightly
The price is $722
Aug 11 - Aug 12
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
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

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

10/10 Excellent
"Beautiful room, friendly staff, nice gym, tasty breakfast…what more do you need?"
William 2-night trip
Posted 4 hours ago
Holiday Inn Express & Suites Middletown by IHG

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.

Explore a world of travel with Expedia

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. Kick off your shoes and enjoy yourself 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 Frightland, or get out into nature at a spot like Betterton Beach. In the larger area, you’ll find Crow Farm and Vineyard and Middletown Town Hall.

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.