Massey Vacation Rentals

Q: 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.

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Dates

November 2026

December 2026

Check prices for these dates

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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

Millington

Quinton

$110 nightly

Nov 9 - Nov 10

Total with taxes and fees

A garden with a wooden bridge, lush greenery, and a variety of plants.

2. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

$253 nightly

Nov 7 - Nov 8

Total with taxes and fees

A spacious living area with a dining table, sofa, and a kitchen in the background.

3. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

$290 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

4. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Middletown

$274 nightly

Nov 13 - Nov 14

Total with taxes and fees

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

$136 nightly

Nov 9 - Nov 10

Total with taxes and fees

6. Bohemia Manor Farm

Chesapeake City

$587 nightly

Nov 14 - Nov 15

Total with taxes and fees

A riverside dock with boats, a covered seating area, and a bridge in the background.

7. Historic Chesapeake City Stay

Chesapeake City

John P.

$270 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

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

Chesapeake City

John

$253 nightly

Nov 30 - Dec 1

Total with taxes and fees

A wooden staircase leading to a beach with a clear view of the sea.

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

Betterton

$317 nightly

Nov 30 - Dec 1

Total with taxes and fees

A covered porch with a wooden bench, potted plants, and a decorative railing.

10. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

$420 nightly

Nov 8 - Nov 9

Total with taxes and fees

A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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

Chestertown

"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...

Miriam G.

$257 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

12. Turtle Cove Room

Kent County

Jennifer M.

$176 nightly

Nov 9 - Nov 10

Total with taxes and fees

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

13. Beachcomber Suite

Kent County

"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...

Lisa E.

$183 nightly

Nov 9 - Nov 10

Total with taxes and fees

A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

14. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Dover

Richard B.

$138 nightly

Nov 11 - Nov 12

Total with taxes and fees

A wooden cabin with a porch, surrounded by dense forest.

15. Country Get Away Studio Apartment

Elkton

JAMES V.

$97 nightly

Nov 16 - Nov 17

Total with taxes and fees

A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

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

Bear

Justin M.

$259 nightly

Nov 8 - Nov 9

Total with taxes and fees

A covered deck area with a grill and outdoor seating.

17. Nature's Haven Tiny Home

Bear

Maxwell

$215 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden deck with lounge chairs and a dock extending into calm water.

18. Waterfront house with amazing views. Top of the Chesapeake

Perryville

Lee Anne K.

$481 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Charlestown

Laura K.

$401 nightly

Nov 9 - Nov 10

Total with taxes and fees

A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

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

Charlestown

Mike F.

$442 nightly

Nov 9 - Nov 10

Total with taxes and fees

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Find vacation rentals that suit your style

Top Massey Hotel Reviews

A lobby area with seating, a reception desk, and a refrigerator stocked with beverages.

Holiday Inn Express & Suites Middletown by IHG

Middletown

10/10 Excellent

Alexander

A modern building with a patio area featuring outdoor seating and a fire pit.

Fairfield Inn & Suites by Marriott Middletown

Middletown

10/10 Excellent

Anonymous traveler

An indoor swimming pool with clear blue water, a tiled deck, and a view of the outside building.

Hampton Inn Middletown

Middletown

10/10 Excellent

Bing

A hotel lobby with a fireplace, seating area, and a television.

Comfort Inn & Suites Chestertown

Chestertown

10/10 Excellent

Laura

A modern lobby with a grey sofa, blue armchairs, and a small table. There are artwork on the walls and a map.

Holiday Inn Express Hotel & Suites Dover by IHG

Dover

10/10 Excellent

Melissa

A modern grocery store with refrigerated sections for chilled and frozen items, shelves stocked with beverages, and a coffee machine.

Hilton Garden Inn Dover

Dover

10/10 Excellent

Karen

A modern dining area with a long table, multiple chairs, and pendant lighting.

Hampton Inn Dover

Dover

10/10 Excellent

Anonymous traveler

A hotel room with a sofa, armchair, ottoman, two side tables with lamps, a coffee table, a TV, and a window with curtains.

Quality Inn Smyrna

Smyrna

10/10 Excellent

What I did not like was the fact that I had to pay $100.00 deposit that nobody mentioned until I got there. and then it may take up to 3 to 5 days to get it back. So I had to go across the street and get $100 cash at 10:00 at night just so I can have my money back immediately. Never heard of such a thing...especially a tiny town like Smyrna...REALLY??? For all its good things, I would not stay there again just based on the inconvenience of a deposit that you may eventually get back. If you got...

RHONDA

A spacious lobby with a central fountain, a grand chandelier, and a curved staircase.

Bally's Dover Casino Resort

Dover

10/10 Excellent

Kimberly

A hotel room with a bed, a sofa, a desk, and a TV.

Comfort Inn & Suites Dover near Speedway

Dover

10/10 Excellent

I really love, the young man who check us in. He was very friendly, and made sure we had what we needed & needed to know. Due to COVID lobby stay clean. Housekeeper: what I dislike was the half clean all the mirrors were marked up and that makes me feel like other things weren't wiped down from being experienced of housekeeping myself, but other than that, my bed was clean, toliet & tub. Setup was nice for walk-in

Dana

A lobby with a sofa, two armchairs, a coffee table, and a floor lamp. There is a painting on the wall and a door leading outside.

Sleep Inn & Suites Dover University Area

Dover

10/10 Excellent

ronald

A sunroom with white wicker furniture, large windows, and a ceiling fan.

Miller-Dunham House Bed & Breakfast

Odessa

10/10 Excellent

Kelly

A patio area with outdoor seating, a fire feature, and a stone wall.

Residence Inn Marriott Dover

Dover

10/10 Excellent

This was my first time staying at a Residence Inn. It was tucked away behind the Fairfield Inn (also owned by Marriot) and it was difficult to see directly from the road. However, once inside, we were greeted by an exceptionally friendly and welcoming staff. I explained that I was there to visit my sick father in the hospital which the front desk person empathized. I really appreciated this. The place was clean, holiday decorated and felt safe. Breakfast was delicious and warm. Breakfast staff...

Tracey

An outdoor seating area with a fire pit, lounge chairs, and a covered patio.

Home2 Suites by Hilton Dover, DE

Dover

10/10 Excellent

Reginald

A hotel room with a large bed, a black leather sofa, a wooden table, two bedside tables with lamps, and a wall-mounted air conditioner.

Relax Inn Smyrna Dover Coastal Gateway

Smyrna

10/10 Excellent

Anonymous traveler

A MainStay Suites hotel with a covered entrance, brick facade, and a clear blue sky.

MainStay Suites Dover

Dover

10/10 Excellent

Anonymous traveler

A lobby with a stone wall, a flat-screen TV, framed pictures, blue sofas, a fireplace, and a wooden bookshelf.

Comfort Suites Dover University Area

Dover

10/10 Excellent

Jordan

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 $102 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.

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.

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