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

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

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

1. Holiday Inn Express & Suites Middletown by IHG

Middletown

Hamlet

฿3,195

฿3,547 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 modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

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

2. Fairfield Inn & Suites by Marriott Middletown

Middletown

Sharon

฿3,994

฿4,434 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 large, beige hotel with a flat roof and symmetrical facade, featuring a central entrance with a covered walkway.

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

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

3. Hampton Inn Middletown

Middletown

DeShun

฿3,459

฿3,840 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 reception desk with a sign reading "Quality Inn" and a potted plant beside it.

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.

4. Quality Inn Smyrna

Smyrna

Tonya

฿3,157

฿3,504 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

5. Comfort Inn & Suites Chestertown

Chestertown

Amy

฿3,281

฿3,642 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 modern lounge area with sofas and a large mural of a tropical landscape.

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

6. Bally's Dover Casino Resort

Dover

michael

฿2,719

฿3,689 total

includes taxes & fees

18 Oct - 19 Oct

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.

7. Hilton Garden Inn Dover

Dover

Elizabeth

฿4,101

฿4,552 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 building with a well-maintained lawn, a tree, and several shrubs.

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

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

8. Sleep Inn & Suites Dover University Area

Dover

James E.

฿2,830

฿3,142 total

includes taxes & fees

5 Nov - 6 Nov

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

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

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

9. Comfort Inn & Suites Dover near Speedway

Dover

Victoria

฿2,906

฿3,226 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.

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

A modern hotel room with a dining area, a sofa, a TV, and a kitchen area.

10. Home2 Suites by Hilton Dover, DE

Dover

Kris

฿4,346

฿4,824 total

includes taxes & fees

10 Nov - 11 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 modern dining area with a long table, blue chairs, and a coffee station.

11. Holiday Inn Express Hotel & Suites Dover by IHG

Dover

Susan

฿3,532

฿3,920 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

12. Fairfield Inn & Suites by Marriott Dover

Dover

Richard

฿3,006

฿3,337 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a wooden desk, a television, a chair, and a lamp.

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

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

13. Hampton Inn Dover

Dover

DINA

฿3,624

฿4,022 total

includes taxes & fees

28 Oct - 29 Oct

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

A hotel with a central entrance, multiple floors, and a flagpole with an American flag.

An indoor swimming pool with clear water, sunlit by large windows, and equipped with lounge chairs and a changing room.

A spacious lobby with teal armchairs, a striped ottoman, and a fireplace.

14. Residence Inn Marriott Dover

Dover

Althia

฿3,969

฿4,406 total

includes taxes & fees

1 Nov - 2 Nov

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

A multi-story brick building with a covered entrance and a parking lot.

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

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

15. Red Roof Inn & Suites Chestertown

Chestertown

Kate

฿2,417

฿2,682 total

includes taxes & fees

22 Oct - 23 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 bar area with a Corona sign, various liquor bottles, a sign indicating a margarita of the day, and a peach garnish.

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

16. Wyndham Garden Dover

Dover

Karla

฿2,417

฿2,683 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

A MainStay Suites reception desk with a dark wood finish, a counter with a marble top, and a wall-mounted display of amenities.

17. MainStay Suites Dover

Dover

RACHELLE

฿3,116

฿3,459 total

includes taxes & fees

15 Nov - 16 Nov

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 bathroom with a toilet, sink, and towel rack.

A hotel room with a flat-screen TV mounted on the wall, a minibar, a desk with a lamp, a chair, and a door.

18. Pleasant Hill Motel

Middletown

฿2,853

฿3,167 total

includes taxes & fees

19 Oct - 20 Oct

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

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.

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

19. Comfort Suites Dover University Area

Dover

Raena

฿2,585

฿2,869 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

20. Relax Inn Smyrna Dover Coastal Gateway

Smyrna

Emily

฿2,987

฿3,824 total

includes taxes & fees

19 Oct - 20 Oct

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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."

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

฿2,371

฿2,632 total

1 Nov - 2 Nov

includes taxes & fees

7.4/10 Good! (1,007 reviews)

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

฿2,417

฿2,682 total

22 Oct - 23 Oct

includes taxes & fees

7.2/10 Good! (509 reviews)

Comfort Suites Dover University Area

1654 N Dupont Hwy Dover DE

฿2,585

฿2,869 total

8 Nov - 9 Nov

includes taxes & fees

Comfort Inn & Suites Dover near Speedway

764 Dover Leipsic Road Dover DE

฿2,906

฿3,226 total

5 Nov - 6 Nov

includes taxes & fees

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

฿3,281

฿3,642 total

8 Nov - 9 Nov

includes taxes & fees

Holiday Inn Express Hotel & Suites Dover by IHG

1780 N Dupont Hwy Dover DE

฿3,532

฿3,920 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 ฿2,632

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. Quality Inn Smyrna

5. Comfort Inn & Suites Chestertown

6. Bally's Dover Casino Resort

7. Hilton Garden Inn Dover

8. Sleep Inn & Suites Dover University Area

9. Comfort Inn & Suites Dover near Speedway

10. Home2 Suites by Hilton Dover, DE

11. Holiday Inn Express Hotel & Suites Dover by IHG

12. Fairfield Inn & Suites by Marriott Dover

13. Hampton Inn Dover

14. Residence Inn Marriott Dover

15. Red Roof Inn & Suites Chestertown

16. Wyndham Garden Dover

17. MainStay Suites Dover

18. Pleasant Hill Motel

19. Comfort Suites Dover University Area

20. Relax Inn Smyrna Dover Coastal Gateway

Top Massey Hotel Reviews

Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express & Suites Middletown by IHG

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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