Massey Holiday Rentals, Maryland: Private House Rentals

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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 hotel lobby with a sofa, armchairs, a small table, a desk with a computer, and a TV.

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

Rp1.700.785

Rp1.887.871 total

includes taxes & fees

15 Nov - 16 Nov

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

A modern living room with a stone accent wall, a flat-screen TV, a dining area with a table and chairs, and a sofa with cushions.

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

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

2. Fairfield Inn & Suites by Marriott Middletown

Middletown

Sharon

Rp2.130.457

Rp2.364.807 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel dining area with a long wooden table, six chairs, and a fruit bowl.

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

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

3. Hampton Inn Middletown

Middletown

DeShun

Rp1.841.324

Rp2.043.869 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A modern lounge area with sofas and a large mural of a tropical landscape.

4. Bally's Dover Casino Resort

Dover

michael

Rp1.449.739

Rp1.967.211 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

5. Comfort Inn & Suites Chestertown

Chestertown

Amy

Rp1.746.617

Rp1.938.745 total

includes taxes & fees

8 Nov - 9 Nov

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 two beds, a TV, a desk, and a window with curtains.

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

A reception desk with a sign reading "Quality Inn" and a potted plant beside it.

6. Quality Inn Smyrna

Smyrna

Tonya

Rp1.683.495

Rp1.868.680 total

includes taxes & fees

25 Oct - 26 Oct

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

A Hilton Garden Inn with a modern design, featuring a large entrance and multiple floors.

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.

7. Hilton Garden Inn Dover

Dover

Elizabeth

Rp2.187.389

Rp2.428.002 total

includes taxes & fees

25 Oct - 26 Oct

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 entrance with a 'Sleep' sign, a 'Clearance Rd' sign, and a '1784' sign.

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

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

8. Sleep Inn & Suites Dover University Area

Dover

James E.

Rp1.506.537

Rp1.672.256 total

includes taxes & fees

5 Nov - 6 Nov

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

A hotel room with a bed, a desk with a computer, a couch, and a television.

An indoor swimming pool with a clear view of the ceiling, walls, and a seating area with chairs.

A modern indoor seating area with wooden flooring, cushioned seating, and potted plants.

9. Home2 Suites by Hilton Dover, DE

Dover

Kris

Rp2.343.503

Rp2.601.288 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A reception desk with two computer monitors, a wooden reception area, and a large wall clock.

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

10. Comfort Inn & Suites Dover near Speedway

Dover

Victoria

Rp1.546.560

Rp1.716.682 total

includes taxes & fees

5 Nov - 6 Nov

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.

An outdoor patio with a fire pit, seating, and umbrellas.

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

11. Holiday Inn Express Hotel & Suites Dover by IHG

Dover

Susan

Rp1.879.815

Rp2.086.594 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

12. Red Roof Inn & Suites Chestertown

Chestertown

Kate

Rp1.288.639

Rp1.430.388 total

includes taxes & fees

27 Oct - 28 Oct

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

An outdoor patio with two round tables, four chairs, two large umbrellas, a barbecue grill, and a swimming pool in the background.

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

13. Hampton Inn Dover

Dover

DINA

Rp1.932.629

Rp2.145.218 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

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

14. Pleasant Hill Motel

Middletown

Rp1.521.500

Rp1.688.865 total

includes taxes & fees

20 Oct - 21 Oct

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

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

A brick building with a white door labeled 'OFFICE,' a fire extinguisher mounted on the wall, and two flower planters on the sidewalk.

15. Relax Inn Smyrna Dover Coastal Gateway

Smyrna

Emily

Rp1.593.100

Rp2.039.168 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

A hotel lobby with a reception desk, two sofas, a coffee table, and a patterned carpet.

16. Wyndham Garden Dover

Dover

Karla

Rp1.288.800

Rp1.430.568 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

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

17. Fairfield Inn & Suites by Marriott Dover

Dover

Richard

Rp1.600.170

Rp1.776.189 total

includes taxes & fees

8 Nov - 9 Nov

A snow-covered porch with a sign for 'Inn at the Canal' and a Christmas tree.

A dining room with a wooden table, chairs, a cabinet with glass doors, and a large window with curtains.

A four-poster bed with floral bedding, a green armchair, and a patterned wall hanging.

A view through a window of a river with a large ship docked at a pier, a sailboat, and a small building with a green roof.

18. Inn At The Canal Bed & Breakfast

Chesapeake City

Jennifer

Rp3.339.961

Rp3.540.359 total

includes taxes & fees

22 Oct - 23 Oct

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

A dining area with tables and chairs, a fireplace, a television, and a kitchen counter with a refrigerator and coffee machine.

A hotel room with two beds, a desk, a chair, and a small table.

A hotel room with a sofa, a small table, a bed, a kitchenette, and a bathroom visible through an open door.

19. MainStay Suites Dover

Dover

RACHELLE

Rp1.658.713

Rp1.841.172 total

includes taxes & fees

15 Nov - 16 Nov

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

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

A hotel reception area with a stone wall, a clock, a cash register, and a phone.

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

20. Comfort Suites Dover University Area

Dover

Raena

Rp1.375.667

Rp1.526.991 total

includes taxes & fees

8 Nov - 9 Nov

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Top Massey Hotel Reviews

Red Roof Inn & Suites Chestertown

8/10 Good

"The place was a little better than average, I'd stay here again. The room smelled musty as if it used to be a smoking room, but not completely unbearable. The desk help was not friendly but not rude either...kind of robotic. Easy parking, roomy room. Decent shower."

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

Rp1.261.771

Rp1.400.566 total

5 Nov - 6 Nov

includes taxes & fees

7.4/10 Good! (1,007 reviews)

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Rp1.288.639

Rp1.430.388 total

27 Oct - 28 Oct

includes taxes & fees

7.2/10 Good! (510 reviews)

Comfort Suites Dover University Area

1654 N Dupont Hwy Dover DE

Rp1.375.667

Rp1.526.991 total

8 Nov - 9 Nov

includes taxes & fees

Comfort Inn & Suites Dover near Speedway

764 Dover Leipsic Road Dover DE

Rp1.546.560

Rp1.716.682 total

5 Nov - 6 Nov

includes taxes & fees

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Rp1.746.617

Rp1.938.745 total

8 Nov - 9 Nov

includes taxes & fees

Holiday Inn Express Hotel & Suites Dover by IHG

1780 N Dupont Hwy Dover DE

Rp1.879.815

Rp2.086.594 total

1 Nov - 2 Nov

includes taxes & fees

Frequently asked questions

What's the best place for a stay in Massey?

Bally's Dover Casino Resort, located 17.7 mi (28.4 km) from the heart of Massey, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Red Roof Inn & Suites Dover Downtown and Comfort Inn & Suites Dover near Speedway. See all available top hotels, or vacation rentals in Massey.

If I need to cancel my hotel reservation in Massey, will I receive a refund?

Yes! Most hotel room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Massey.

What is staying in Massey like?

Visitors to Massey will definitely find plenty to explore and enjoy. There are 333 hotels and other accommodation options in the surrounding area. Find out more about Massey.

What should I see while I'm in Massey?

Places to visit in the wider area include Middletown Town Hall, Middletown Historic District and Bohemia Bay Yacht Harbour. You'll also find Bohemia Vista Marina and Betterton Beach in the area. Take a look at what more there is to see and do in Expedia's Massey guide.

What's the weather like in Massey?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Massey is 1359 mm.

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Book Hotels in Massey on Expedia.com

Find hotels in Massey, MD from Rp1.400.566

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Massey

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Massey hotels

1. Holiday Inn Express & Suites Middletown by IHG

2. Fairfield Inn & Suites by Marriott Middletown

3. Hampton Inn Middletown

4. Bally's Dover Casino Resort

5. Comfort Inn & Suites Chestertown

6. Quality Inn Smyrna

7. Hilton Garden Inn Dover

8. Sleep Inn & Suites Dover University Area

9. Home2 Suites by Hilton Dover, DE

10. Comfort Inn & Suites Dover near Speedway

11. Holiday Inn Express Hotel & Suites Dover by IHG

12. Red Roof Inn & Suites Chestertown

13. Hampton Inn Dover

14. Pleasant Hill Motel

15. Relax Inn Smyrna Dover Coastal Gateway

16. Wyndham Garden Dover

17. Fairfield Inn & Suites by Marriott Dover

18. Inn At The Canal Bed & Breakfast

19. MainStay Suites Dover

20. Comfort Suites Dover University Area

Top Massey Hotel Reviews

Red Roof Inn & Suites Chestertown

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

Frequently asked questions

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