Top 10 Hotels in Massey, MD (from $78) 2026 - Competitive Prices

Go beyond your typical stay in Massey

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Our top choices for Massey hotels

A modern building with a covered entrance, stone pillars, and a parking lot with cars.

A hotel room with a coffee machine, a bed, and a window with a view.

A modern restaurant with booths and tables, a TV screen displaying AT&T, and a wooden ceiling.

A reception area with two reception desks, a glass partition, and a wall with geometric patterns.

1. Holiday Inn Express & Suites Middletown by IHG

Middletown

Hamlet

$95 nightly

$105 total

Nov 15 - Nov 16

Total with taxes and fees

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

A large, beige hotel with a flat roof and symmetrical facade, featuring a central entrance with a covered walkway.

A gym with treadmills, an elliptical, and a wall of dumbbells.

A hotel room with a large bed, a desk with a TV, a red chair, and a window with curtains.

2. Hampton Inn Middletown

Middletown

DeShun

$103 nightly

$114 total

Nov 8 - Nov 9

Total with taxes and fees

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

A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.

A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

3. Fairfield Inn & Suites by Marriott Middletown

Middletown

Sharon

$119 nightly

$132 total

Nov 1 - Nov 2

Total with taxes and fees

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

A hotel room with a sofa, a TV on a wooden stand, a lamp, and a door leading to another room.

A breakfast buffet with a variety of food items and a bowl of fruit.

A hotel room with two beds, a TV, a desk, and a window with curtains.

4. Quality Inn Smyrna

Smyrna

Tonya

$94 nightly

$104 total

Oct 25 - Oct 26

Total with taxes and fees

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

5. Comfort Inn & Suites Chestertown

Chestertown

Amy

$98 nightly

$108 total

Nov 8 - Nov 9

Total with taxes and fees

A hotel room with a sofa, two beds, a painting, and a lamp.

A living room with a fireplace, a television, and a stone accent wall.

A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.

A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

6. Red Roof Inn & Suites Chestertown

Chestertown

Kate

$72 nightly

$80 total

Oct 22 - Oct 23

Total with taxes and fees

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.

A hotel lobby with a reception desk, seating area, and a dining section in the background.

A building with a well-maintained lawn, a tree, and several shrubs.

A hotel room with two beds, a sofa, a lamp, and wall art.

7. Sleep Inn & Suites Dover University Area

Dover

James E.

$84 nightly

$93 total

Nov 5 - Nov 6

Total with taxes and fees

A hotel room with two beds, each with floral bedding, a large mirror, and two wall-mounted lamps.

A bathroom with a toilet, sink, and shower curtain.

A hotel room with two beds, a nightstand, a mirror, and two wall-mounted lamps.

A bathroom with a toilet, sink, and towel rack.

8. Pleasant Hill Motel

Middletown

$76 nightly

$84 total

Oct 19 - Oct 20

Total with taxes and fees

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

A modern bar area with three blue bar stools, a large selection of bottles and glasses on shelves, and pendant lighting.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and potted plants.

A modern kitchen with a central island, bar stools, and a variety of appliances including a coffee maker and a toaster.

9. Hilton Garden Inn Dover

Dover

Elizabeth

$122 nightly

$136 total

Oct 25 - Oct 26

Total with taxes and fees

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

A spacious dining area with multiple tables and chairs, a coffee machine, and a refrigerator.

A hotel room with a sofa, two ottomans, a bed with a green blanket, a nightstand with a lamp, and a large wooden headboard.

A gym with cardio machines, dumbbells, and a bench.

10. Comfort Suites Dover University Area

Dover

Raena

$77 nightly

$85 total

Nov 8 - Nov 9

Total with taxes and fees

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

A Holiday Inn Express hotel with a covered entrance and a brick facade.

A reception area with two wooden reception desks, a blue geometric wall, and a potted plant.

A modern dining area with a long table, blue chairs, and a coffee station.

11. Holiday Inn Express Hotel & Suites Dover by IHG

Dover

Susan

$105 nightly

$117 total

Nov 1 - Nov 2

Total with taxes and fees

A snack display with various brands and a refrigerated section with beverages.

A hotel room with a bed, a desk, a chair, a television, and a window with curtains.

A hotel corridor with a checkered floor, a coffee machine, a clock, and a bakery counter.

12. Hampton Inn Dover

Dover

DINA

$108 nightly

$120 total

Oct 28 - Oct 29

Total with taxes and fees

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.

A parking lot with a rainbow, a building with a billboard, and a grassy area.

A room with a window displaying a menu, a sign indicating check-in and check-out times, and a chair.

A bathroom with a toilet, a towel rack, and a toilet paper dispenser.

13. Relax Inn Smyrna Dover Coastal Gateway

Smyrna

Emily

$107 nightly

$114 total

Oct 18 - Oct 19

Total with taxes and fees

A row of motel rooms with stone walls and red doors.

A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

A two-story building with a brick facade, large windows, and a sloped roof.

A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

14. Driftwood Inn

Chestertown

Kathy

$64 nightly

$70 total

Oct 16 - Oct 17

Total with taxes and fees

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

A storefront with a sign reading "Jerry Longo's meatballs & martinis."

A round wooden table with four plates of food, cutlery, and glasses.

A group of people seated at a table in a covered outdoor area with a view of a forested landscape.

15. Bally's Dover Casino Resort

Dover

michael

$110 nightly

$120 total

Oct 18 - Oct 19

Total with taxes and fees

A modern lobby with a reception desk, seating area, and a colorful carpet.

A modern living room with a stone fireplace, blue chairs, a patterned rug, and a large window with sheer curtains.

A hotel lobby with a reception desk, a clock, a colorful abstract painting, and a reception area with a counter and cabinets.

A multi-story Fairfield by Marriott Inn & Suites building with a prominent entrance, a covered outdoor area, and a parking lot.

16. Fairfield Inn & Suites by Marriott Dover

Dover

Richard

$89 nightly

$99 total

Nov 8 - Nov 9

Total with taxes and fees

A modern hotel with a covered entrance, stone pillars, and a well-lit facade.

A bar area with a Corona sign, various liquor bottles, a sign indicating a margarita of the day, and a peach garnish.

A restaurant interior with wooden flooring, booths, and tables.

A hotel room with a large bed, a desk with a lamp, and a door leading to the bathroom.

17. Wyndham Garden Dover

Dover

Karla

$72 nightly

$80 total

Oct 18 - Oct 19

Total with taxes and fees

A hotel room with a bed, a chair, a desk, and a painting on the wall.

A coffee station with a coffee maker, cups, and coffee creamer dispensers.

A compact living space with a sofa, a small table, a kitchenette, and a door.

Two vending machines, one labeled 'COLD DRINKS' and the other with a variety of snacks and drinks.

18. Red Roof Inn & Suites Dover Downtown

Dover

Dieunata

$70 nightly

$78 total

Nov 1 - Nov 2

Total with taxes and fees

A street view with a motel sign, a building with a number 1760, and parked cars.

A bathroom with a bathtub, a toilet, and a microwave.

A hotel room with a large bed, a nightstand with a lamp, a chair, and a window with curtains.

A Holiday Inn Express & Suites with a parking lot, a building with a sign for the inn, and a McDonald's across the street.

19. First State Inn

Dover

Andrea

$77 nightly

$85 total

Oct 18 - Oct 19

Total with taxes and fees

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

A spacious living room with a blue sofa set, a fireplace, a staircase with a patterned carpet, and a framed eye chart on the wall.

A Comfort Inn & Suites hotel with a covered parking area and a landscaped entrance.

A hotel room with a sofa, a desk with a chair, a lamp, and framed pictures on the wall.

20. Comfort Inn & Suites Dover near Speedway

Dover

Victoria

$88 nightly

$98 total

Nov 5 - Nov 6

Total with taxes and fees

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Where to stay near Massey

Massey, Maryland, offers a delightful blend of outdoor adventures and family-friendly activities. Explore charming nearby towns with rich history, beautiful scenery, and friendly locals. Whether you're seeking adventure or relaxation, the region promises a memorable experience for all travelers.

Galena

Discover Galena, a welcoming destination perfectly suited for families and adventure seekers who will appreciate its charming blend of outdoor activities and cultural experiences. With attractions like the scenic Skipjack Cove Yachting Resort, the historic Galena Town Hall, and the relaxing Galena Town Park, there's plenty to explore. Located about 4 miles from Massey, Galena offers a great choice for travelers looking to enjoy a memorable stay in a picturesque setting.

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Millington

Experience the charm of Millington, an excellent hub for travelers seeking a blend of business, family, and nature. This inviting city offers access to outdoor adventures at Pinkney Park and the scenic beauty of nearby beaches and state parks. Visitors can also enjoy the unique atmosphere of Crumpton Auction and explore the recreational opportunities at Crumpton Park. Located about 4 miles by car from Massey, Millington is a smart choice for your next vacation getaway.

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A steel arch bridge over a river with surrounding trees and buildings.

An aerial view of a historic town with distinct architectural styles, including a church with a golden dome and a large brick building with a flat roof.

A bridge with multiple yellow cables and a clear blue sky.

Middletown

Make the most of your visit by staying in Middletown, a haven for family travelers thanks to its blend of outdoor activities and city experiences. Explore the charming Middletown Historic District, visit the Historic Houses of Odessa, and enjoy the vibrant shopping centers that cater to all ages. Located about 15 miles away from Massey, Middletown offers easy access for a weekend getaway or a longer vacation. Choosing Middletown means embracing a delightful mix of history and convenience.

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Cecilton

Immerse yourself in Cecilton, where families and nature enthusiasts can easily access beautiful parks, scenic hiking trails, and exciting motor racing activities. Just a short distance from Massey, this charming city invites visitors to explore attractions like the Bohemia Vista Marina and Church Street Park, perfect for outdoor adventures. With visitor numbers peaking in spring and summer, Cecilton offers a vibrant atmosphere year-round, making it a smart choice for your next getaway.

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Crumpton

Travelers visiting the area often choose Crumpton, especially families and nature enthusiasts seeking a tranquil getaway. This charming city offers delightful experiences with its beautiful bay, scenic beach, and recreational spots like Pinkney Park. Visitors can also explore the historic Washington College, making it a perfect blend of relaxation and education. Located about 11 miles by car from Massey, Crumpton is a smart choice for a memorable vacation, providing budget-friendly options and plenty of outdoor activities.

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Stay near popular attractions around Massey

Massey invites you to immerse yourself in its vibrant outdoor scene, perfect for family adventures and city getaways. Explore beautiful parks and marinas that offer endless opportunities for fun and relaxation, making it an ideal base for your next memorable vacation.

Mount Harmon Plantation

8.0/10 (3 reviews)

Set the stage for your exploration of Mount Harmon Plantation, a historic gem in Earleville, Maryland, perfect for history buffs. This plantation offers a glimpse into the past with its rich cultural vibes. Located about 8 miles from Massey, it's an easily accessible site for a memorable visit.

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A field of soybeans with a barn and silos in the background.

Washington College

8.6/10 (87 reviews)

No trip is complete without a visit to Washington College, a historic institution nestled in Chestertown, Maryland. Known for its rich culture and vibrant campus life, it offers a unique glimpse into American academic heritage. It's about a 19-mile drive from Massey, making it a convenient stop for visitors exploring the area.

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A white lighthouse with a black top and a small door at the base, surrounded by grass and trees.

Elk Neck State Park

8.6/10 (34 reviews)

Enjoy the simplicity of Elk Neck State Park, a haven for outdoor lovers seeking adventure and stunning scenery. With its picturesque trails and diverse wildlife, it offers a unique escape into nature. Located about 14 miles from Massey, this park makes for a convenient day trip for your vacation.

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Crumpton Auction

8.8/10 (3 reviews)

Ideal for families seeking a unique outing, Crumpton Auction offers a charming blend of local culture and recreational fun. Located about 7 miles from Massey, this lively attraction provides an engaging experience, making it a convenient stop for those exploring the area.

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Bohemia Vista Marina

10.0/10 (3 reviews)

Highly recommended for outdoor adventurers, Bohemia Vista Marina offers a scenic escape with its beautiful beach and vibrant atmosphere. Located about 13 miles from Massey, it's an ideal spot for enjoying water activities and soaking up the sun, making it a convenient choice for your stay in the area.

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Betterton Beach

Discover the appeal of Betterton Beach, a hidden gem perfect for beach lovers seeking relaxation and scenic views. With its inviting beach vibes, this destination offers a refreshing escape. It’s an easy drive of about 18 miles from Massey, making it a convenient choice for a day by the water.

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Historic Houses of Odessa

8.0/10 (5 reviews)

Perfectly suited for history buffs, the Historic Houses of Odessa offers a captivating glimpse into the region's rich cultural heritage. Located about 20 miles by car from Massey, this charming site showcases beautifully preserved homes that reflect the area’s architectural evolution. Staying nearby provides easy access to these fascinating landmarks.

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Back Creek Golf Club

9.2/10 (7 reviews)

A must-see for golf lovers, Back Creek Golf Club offers a welcoming atmosphere and budget-friendly vibes in Middletown, Delaware. With its lush greens and scenic views, it's perfect for a day on the course. Located about 14 miles from Massey, it's an easy trip for a memorable golfing experience.

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Top Massey Hotel Reviews

Fairfield Inn & Suites by Marriott Middletown

8/10 Good

"Hotel was great. Really nice. loved having doormen considering area is not great. Just wished"

Holiday Inn Express & Suites Middletown by IHG

8/10 Good

"Friendly staff. Breakfast was adequate. Parking was close."

Red Roof Inn & Suites Dover Downtown

10/10 Excellent

"Great. Just an overnight stay"

Sleep Inn & Suites Dover University Area

8/10 Good

"Room card did not work, we had to go to the front desk every time that we need to get into the room, because the card did not work at the room door."

Home2 Suites by Hilton Dover, DE

10/10 Excellent

"I like the layout of the kitchen area and the available kitchen ware - plates, glasses, utensils"

DOVER INN

10/10 Excellent

"Very helpful staff, need to fix their phone."

Hampton Inn Middletown

10/10 Excellent

"The male employee working night shift hours on 10/03/2026 was more than accommodating and polite."

More cheap stays in Massey

Red Roof Inn & Suites Dover Downtown

652 N Dupont Hwy Dover DE

$70 nightly

$78 total

Nov 1 - Nov 2

Total with taxes and fees

7.4/10 Good! (1,007 reviews)

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

$72 nightly

$80 total

Oct 22 - Oct 23

Total with taxes and fees

7.2/10 Good! (509 reviews)

Comfort Suites Dover University Area

1654 N Dupont Hwy Dover DE

$77 nightly

$85 total

Nov 8 - Nov 9

Total with taxes and fees

Comfort Inn & Suites Dover near Speedway

764 Dover Leipsic Road Dover DE

$88 nightly

$98 total

Nov 5 - Nov 6

Total with taxes and fees

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

$98 nightly

$108 total

Nov 8 - Nov 9

Total with taxes and fees

Holiday Inn Express Hotel & Suites Dover by IHG

1780 N Dupont Hwy Dover DE

$105 nightly

$117 total

Nov 1 - Nov 2

Total with taxes and fees

Hotels in Massey with star-rating

Frequently asked questions

When is the best time to go to Massey?

The best time to go to Massey is during the spring (April to May) and fall (September to October) months when the weather is pleasant and comfortable for outdoor activities.Spring in Massey brings mild temperatures, typically ranging from the 50s to 70s Fahrenheit (10-25°C). This season is ideal for exploring the natural beauty of the Eastern Shore, with blooming wildflowers and lush greenery. It's a great time for couples to enjoy scenic drives along the Chesapeake Country National Scenic Byway or visit local farms.Fall also offers comfortable weather, with temperatures generally from the 50s to 70s Fahrenheit (10-25°C), and the added beauty of changing foliage. This period is superb for solo travelers interested in photography or attending local harvest festivals.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Massey.

How much is the nightly rate at a Massey hotel?

Prices for hotels in Massey often vary, but you can find a great deal from $78 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Find hotels in Massey, MD from $78

Go beyond your typical stay in Massey

Check prices for these dates

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Our top choices for Massey hotels

1. Holiday Inn Express & Suites Middletown by IHG

2. Hampton Inn Middletown

3. Fairfield Inn & Suites by Marriott Middletown

4. Quality Inn Smyrna

5. Comfort Inn & Suites Chestertown

6. Red Roof Inn & Suites Chestertown

7. Sleep Inn & Suites Dover University Area

8. Pleasant Hill Motel

9. Hilton Garden Inn Dover

10. Comfort Suites Dover University Area

11. Holiday Inn Express Hotel & Suites Dover by IHG

12. Hampton Inn Dover

13. Relax Inn Smyrna Dover Coastal Gateway

14. Driftwood Inn

15. Bally's Dover Casino Resort

16. Fairfield Inn & Suites by Marriott Dover

17. Wyndham Garden Dover

18. Red Roof Inn & Suites Dover Downtown

19. First State Inn

20. Comfort Inn & Suites Dover near Speedway

Where to stay near Massey

Galena

Millington

Middletown

Cecilton

Crumpton

Stay near popular attractions around Massey

Mount Harmon Plantation

Washington College

Elk Neck State Park

Crumpton Auction

Bohemia Vista Marina

Betterton Beach

Historic Houses of Odessa

Back Creek Golf Club

Top Massey Hotel Reviews

Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express & Suites Middletown by IHG

Red Roof Inn & Suites Dover Downtown

Sleep Inn & Suites Dover University Area

Home2 Suites by Hilton Dover, DE

DOVER INN

Hampton Inn Middletown

More cheap stays in Massey

Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Chestertown

Comfort Suites Dover University Area

Comfort Inn & Suites Dover near Speedway

Comfort Inn & Suites Chestertown

Holiday Inn Express Hotel & Suites Dover by IHG

Hotels in Massey with star-rating

Frequently asked questions

Explore a world of travel with Expedia