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Massey Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Massey vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (23 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AED 397
AED 1,024 total
includes taxes & fees
30 Jun - 1 Jul
Historic Chesapeake City Stay
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (114 reviews)
"Every thing was great"
United States
lesia k.
The price is AED 364
AED 583 total
includes taxes & fees
30 Jun - 1 Jul
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.
The price is AED 250
AED 459 total
includes taxes & fees
30 Jun - 1 Jul
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, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is AED 257
AED 409 total
includes taxes & fees
6 Jul - 7 Jul
Country Get Away Studio Apartment
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 AED 694
AED 858 total
includes taxes & fees
30 Jun - 1 Jul
Nature's Haven Tiny Home
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, (6 reviews)
The price is AED 441
AED 685 total
includes taxes & fees
12 Jul - 13 Jul
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
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 AED 694
AED 876 total
includes taxes & fees
30 Jun - 1 Jul
Tiny Home Tranquil Oasis
Marina

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
The price is AED 918
AED 1,092 total
includes taxes & fees
1 Jul - 2 Jul
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
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 AED 661
AED 1,025 total
includes taxes & fees
6 Jul - 7 Jul
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.
The price is AED 826
AED 1,391 total
includes taxes & fees
30 Jun - 1 Jul
Waterfront Retreat with Private Dock and Beach
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 516
AED 640 total
includes taxes & fees
27 Jul - 28 Jul
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, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is AED 918
AED 1,415 total
includes taxes & fees
30 Jun - 1 Jul
Newly restored apartment in the heart of Chestertown
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 AED 1,129
AED 1,790 total
includes taxes & fees
1 Jul - 2 Jul
Long Beach Cottage, (romantic couple’s getaway)
Fridge, microwave, oven, dishwasher

Right in the center of everywhere in Dover

Right in the center of everywhere in Dover
Dover
9.0 out of 10, Wonderful, (6 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 AED 826
AED 1,760 total
includes taxes & fees
5 Jul - 6 Jul
Right in the center of everywhere in Dover
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
The price is AED 536
AED 665 total
includes taxes & fees
13 Jul - 14 Jul
Beachcomber Suite
Interior

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
The price is AED 825
AED 1,466 total
includes taxes & fees
1 Jul - 2 Jul
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
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.
The price is AED 1,134
AED 1,537 total
includes taxes & fees
13 Jul - 14 Jul
Elegant Family Stay • Quiet Neighborhood • Comfort
Property grounds

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is AED 661
AED 751 total
includes taxes & fees
1 Jul - 2 Jul
Wren Retweet- Country Estate in Center of C’Town
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 AED 2,141
AED 2,452 total
includes taxes & fees
1 Jul - 2 Jul
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

Quality Inn Smyrna

Quality Inn Smyrna

10/10 Excellent
"The room was clean, the staff was pleasant."
Michelle 1-night trip
Posted 17 hours ago
Quality Inn Smyrna

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 Turner's Creek Park. 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.