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Massey Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (28 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 ￥10,668
￥19,623 total
includes taxes & fees
Sep 22 - Sep 23
Guest Suite for up to 2 in a Victorian on the Chester River
Marina

2. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (29 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 ￥16,943
￥42,737 total
includes taxes & fees
Sep 23 - Sep 24
Historic Chesapeake City Stay
Property grounds

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,531
￥24,919 total
includes taxes & fees
Sep 29 - Sep 30
First Floor Studio Apartment in Historic Chestertown
Exterior

4. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is ￥10,982
￥17,461 total
includes taxes & fees
Sep 28 - Sep 29
Country Get Away Studio Apartment
Interior

5. 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)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is ￥14,119
￥24,167 total
includes taxes & fees
Sep 30 - Oct 1
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
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 ￥26,748
￥33,147 total
includes taxes & fees
Sep 29 - Sep 30
Beachcomber Suite
1 bedroom, WiFi, bed sheets

7. Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥27,297
￥33,745 total
includes taxes & fees
Sep 29 - Sep 30
Turtle Cove Room
Smart TV

8. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is ￥34,514
￥50,720 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
TV, fireplace

9. 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 ￥28,803
￥42,982 total
includes taxes & fees
Sep 23 - Sep 24
Secluded Cottage in Middle of Chestertown
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

10. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
The price is ￥22,591
￥45,731 total
includes taxes & fees
Sep 30 - Oct 1
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Luxury House, Multiple Bedrooms, Lake View | Laptop workspace, WiFi (free)

11. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is ￥54,773
￥58,059 total
includes taxes & fees
Oct 4 - Oct 5
Bohemia Manor Farm
Beach nearby

12. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is ￥27,454
￥47,359 total
includes taxes & fees
Oct 4 - Oct 5
Waterfront Retreat with Private Dock and Beach
Terrace/patio

13. 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 ￥29,650
￥36,633 total
includes taxes & fees
Sep 22 - Sep 23
Nature's Haven Tiny Home
Pool

14. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
The price is ￥25,101
￥40,036 total
includes taxes & fees
Sep 28 - Sep 29
Mini Aruba RV/Glamping Tent
Property grounds

15. 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 ￥47,779
￥75,501 total
includes taxes & fees
Sep 29 - Sep 30
Wren Retweet- Country Estate in Center of C’Town
Interior

16. 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, (4 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 ￥39,220
￥44,593 total
includes taxes & fees
Sep 23 - Sep 24
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Terrace/patio

17. 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 ￥29,650
￥37,888 total
includes taxes & fees
Sep 22 - Sep 23
Tiny Home Tranquil Oasis
Microwave, oven, stovetop, dishwasher

18. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Host was great"
United States
mark o.
The price is ￥37,494
￥85,775 total
includes taxes & fees
Sep 22 - Sep 23
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
TV, fireplace, books

19. 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 ￥44,899
￥72,094 total
includes taxes & fees
Sep 22 - Sep 23
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

Comfort Inn & Suites Dover near Speedway

Comfort Inn & Suites Dover near Speedway

8/10 Good
"housekeeping was poor"
william 3-night trip
Posted 11 hours ago
Comfort Inn & Suites Dover near Speedway

Find out more about Massey

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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. 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 Middletown Town Hall and Middletown Square.

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.