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Massey Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Massey vacation rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
$118 nightly
The price is $125
Oct 28 - Oct 29
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Nov 2 - Nov 3
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

3. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Nov 3 - Nov 4
Total with taxes and fees
Country Get Away Studio Apartment
A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

4. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
$294 nightly
The price is $312
Oct 28 - Oct 29
Total with taxes and fees
Historic Chesapeake City Stay
A garden path leading to a wooden building with a rustic appearance.

5. 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.
$264 nightly
The price is $274
Oct 28 - Oct 29
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

6. 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, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
$181 nightly
The price is $186
Nov 3 - Nov 4
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

7. Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay here! The house was clean, cozy, and had everything we needed. The host was so nice and easy to communicate with, which made everything really easy. We felt right at home and would definitely stay here again!"
United States
Destiny H.
$357 nightly
The price is $371
Oct 29 - Oct 30
Total with taxes and fees
Welcome to the secluded waterfront oasis
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

8. 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.
$197 nightly
The price is $214
Nov 9 - Nov 10
Total with taxes and fees
Beachcomber Suite
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

9. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
$326 nightly
The price is $346
Oct 28 - Oct 29
Total with taxes and fees
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

10. Turtle Cove Room

Turtle Cove Room
Kent County
$185 nightly
The price is $201
Nov 2 - Nov 3
Total with taxes and fees
Turtle Cove Room
A covered outdoor seating area with a wooden ceiling, two chairs, a table, and a wicker sofa.

11. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
$338 nightly
The price is $373
Nov 23 - Nov 24
Total with taxes and fees
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A spacious living area with a dining table, sofa, and a kitchen in the background.

12. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
$320 nightly
The price is $353
Oct 28 - Oct 29
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Restaurant

13. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
$348 nightly
The price is $368
Oct 28 - Oct 29
Total with taxes and fees
Bohemia Manor Farm
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
$270 nightly
The price is $286
Nov 2 - Nov 3
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A covered porch with a wooden bench, potted plants, and a decorative railing.

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.
$463 nightly
The price is $481
Nov 2 - Nov 3
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A covered deck area with a grill and outdoor seating.

16. 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
$225 nightly
The price is $234
Oct 28 - Oct 29
Total with taxes and fees
Nature's Haven Tiny Home
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

17. 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
9.8 out of 10, Exceptional, (7 reviews)
"The host was great and easy to communicate with. It was a first time experience staying on a boat for my family and I and we really enjoyed it. Perfect for a few nights to visit family nearby."
United States
Jessica
$286 nightly
The price is $297
Oct 29 - Oct 30
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

18. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$484 nightly
The price is $507
Nov 9 - Nov 10
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

19. 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, (5 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.
$361 nightly
The price is $376
Oct 28 - Oct 29
Total with taxes and fees
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

20. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
$469 nightly
The price is $497
Nov 2 - Nov 3
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
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

Sleep Inn & Suites Dover University Area

Sleep Inn & Suites Dover University Area

8/10 Good
"Didn’t like that their were no hangers in my room. The toilet was wobbly. The pull out sofa has no sheets or blanket. My key card kept shutting off"
Nicole 2-night trip
Posted 2 hours ago
Sleep Inn & Suites Dover University Area

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 $111 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 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.