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Massey Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Massey vacation rentals

Exterior

1. 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, (26 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
9 Sep - 10 Sep
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (120 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AED 364
AED 583 total
includes taxes & fees
20 Aug - 21 Aug
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is AED 826
AED 1,297 total
includes taxes & fees
19 Aug - 20 Aug
Newly restored apartment in the heart of Chestertown
Marina

4. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is AED 397
AED 1,040 total
includes taxes & fees
16 Aug - 17 Aug
Historic Chesapeake City Stay
Interior

5. 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
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is AED 918
AED 1,084 total
includes taxes & fees
11 Sep - 12 Sep
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Property grounds

6. 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.
The price is AED 586
AED 728 total
includes taxes & fees
24 Aug - 25 Aug
Beachcomber Suite
TV, fireplace

7. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is AED 674
AED 1,037 total
includes taxes & fees
19 Aug - 20 Aug
Secluded Cottage in Middle of Chestertown
Terrace/patio

8. 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 869 total
includes taxes & fees
16 Aug - 17 Aug
Nature's Haven Tiny Home
Exterior

9. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is AED 257
AED 409 total
includes taxes & fees
31 Aug - 1 Sep
Country Get Away Studio Apartment
Terrace/patio

10. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is AED 694
AED 887 total
includes taxes & fees
16 Aug - 17 Aug
Tiny Home Tranquil Oasis
Beach nearby

11. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AED 826
AED 1,390 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
Property grounds

12. 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)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is AED 1,178
AED 1,838 total
includes taxes & fees
1 Sep - 2 Sep
Wren Retweet- Country Estate in Center of C’Town
1 bedroom, WiFi, bed sheets

13. Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 516
AED 640 total
includes taxes & fees
17 Aug - 18 Aug
Turtle Cove Room
Terrace/patio

14. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is AED 1,324
AED 2,068 total
includes taxes & fees
23 Aug - 24 Aug
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Exterior

15. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is AED 1,094
AED 1,511 total
includes taxes & fees
26 Aug - 27 Aug
Elegant Family Stay • Quiet Neighborhood • Comfort
Interior

16. 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, (10 reviews)
"What a wonderful place! It was very clean and is stocked with everything you could need for your stay. We thoroughly enjoyed our time there and would certainly go back whenever we’re in the area. Thank you Kara for sharing part of your home with us."
United States
Susan S.
The price is AED 404
AED 646 total
includes taxes & fees
9 Sep - 10 Sep
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Pool

17. 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 551
AED 903 total
includes taxes & fees
6 Sep - 7 Sep
Mini Aruba RV/Glamping Tent
Sun loungers, beach towels

18. 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, (156 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AED 1,322
AED 2,402 total
includes taxes & fees
15 Sep - 16 Sep
5-bedroom vacation home 5 minutes from historic Charlestown
Interior

19. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is AED 215
AED 353 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Room in Dover
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

8/10 Good
"Room clean, staff pleasant"
Paula 5-night trip
Posted less than an hour ago
Bally's Dover Casino Resort

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?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: Visitors like this Massey vacation home rental. It is located on a lake and has a patio, 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 dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.