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

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

Rp1.704.110

Rp1.891.562 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 fireplace, wooden ceiling, and a large TV mounted above it.

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.

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

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.

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

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

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

4. Bally's Dover Casino Resort

Dover

Rp1.449.982

Rp1.967.541 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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

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

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

Rp1.750.031

Rp1.942.535 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 breakfast buffet with a variety of food items and a bowl of fruit.

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

6. Quality Inn Smyrna

Smyrna

Tonya

Rp1.509.483

Rp1.675.527 total

includes taxes & fees

16 Nov - 17 Nov

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.

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.

7. Hilton Garden Inn Dover

Dover

Elizabeth

Rp2.190.074

Rp2.430.983 total

includes taxes & fees

3 Nov - 4 Nov

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 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.

8. Sleep Inn & Suites Dover University Area

Dover

James E.

Rp1.509.483

Rp1.675.527 total

includes taxes & fees

8 Nov - 9 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.

9. Home2 Suites by Hilton Dover, DE

Dover

Kris

Rp2.317.590

Rp2.572.525 total

includes taxes & fees

25 Oct - 26 Oct

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

Rp1.535.493

Rp1.704.397 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

Rp1.879.815

Rp2.086.595 total

includes taxes & fees

25 Oct - 26 Oct

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.

12. Red Roof Inn & Suites Chestertown

Chestertown

Kate

Rp1.288.855

Rp1.430.628 total

includes taxes & fees

25 Oct - 26 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.

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

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 bathroom with a toilet, sink, and shower curtain.

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

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

14. Pleasant Hill Motel

Middletown

Rp1.521.755

Rp1.689.148 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

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

15. Wyndham Garden Dover

Dover

Karla

Rp1.289.016

Rp1.430.807 total

includes taxes & fees

19 Oct - 20 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 parking lot with a rainbow, a building with a billboard, and a grassy area.

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

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

16. Relax Inn Smyrna Dover Coastal Gateway

Smyrna

Rp1.593.367

Rp2.039.509 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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.

17. Fairfield Inn & Suites by Marriott Dover

Dover

Richard

Rp1.603.298

Rp1.779.661 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 row of historic buildings with a waterfront view, featuring a porch with American flags and a clock.

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

18. Inn At The Canal Bed & Breakfast

Chesapeake City

Rp3.340.521

Rp3.540.953 total

includes taxes & fees

22 Oct - 23 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 dining area with tables and chairs, a fireplace, a television, and a kitchen counter with a refrigerator and coffee machine.

19. MainStay Suites Dover

Dover

RACHELLE

Rp1.661.956

Rp1.844.771 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 spacious dining area with multiple tables and chairs, a coffee machine, and a refrigerator.

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

virginia

Rp1.378.356

Rp1.529.976 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

Rp1.261.982

Rp1.400.800 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

Rp1.288.855

Rp1.430.628 total

25 Oct - 26 Oct

includes taxes & fees

7.2/10 Good! (510 reviews)

Comfort Suites Dover University Area

1654 N Dupont Hwy Dover DE

Rp1.378.356

Rp1.529.976 total

8 Nov - 9 Nov

includes taxes & fees

Comfort Inn & Suites Dover near Speedway

764 Dover Leipsic Road Dover DE

Rp1.535.493

Rp1.704.397 total

16 Nov - 17 Nov

includes taxes & fees

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Rp1.750.031

Rp1.942.535 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

Rp2.086.595 total

25 Oct - 26 Oct

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 Rp1.400.800

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. Wyndham Garden Dover

16. Relax Inn Smyrna Dover Coastal Gateway

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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