Hotels with connecting rooms in Eastern Shore
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Hotels with connecting rooms
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Hotels with connecting rooms in Eastern Shore

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your current months are November, 2026 and December, 2026.

November 2026

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Our top choices for Eastern Shore hotels with connecting rooms

Two Adirondack chairs facing a calm body of water with a clear sky above.

A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

A buffet with various food items, including omelets and baked goods, served in metal containers.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

1. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property

Grasonville

9.2 out of 10, Wonderful, (1,002 reviews)

9.2/10

Wonderful

(1,002 reviews)

"A wonderful stay! Already planning a trip for next year!"

Michelle

The price is S$135

S$135

includes taxes & fees

6 Dec - 7 Dec

Holiday Inn Express Annapolis East-Kent Island by IHG

A resort with a large pool, outdoor seating, and a view of the sea.

A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

A spacious restaurant with high ceilings, large windows, and a variety of seating arrangements.

A marina with boats docked, a sandy beach, and a clear blue sky.

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4.0 star property

Cambridge

8.8 out of 10, Excellent, (1,005 reviews)

8.8/10

Excellent

(1,005 reviews)

"The staff at the front desk were friendly and helpful."

Billy

The price is S$247

S$247

includes taxes & fees

23 Nov - 24 Nov

Hyatt Regency Chesapeake Bay

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

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

A kitchen with a stone wall, a microwave, and various food items on the counter.

A residential area with a large building, a swimming pool, and well-maintained lawns.

3. Baymont by Wyndham Easton

Baymont by Wyndham Easton

2.5 star property

Easton

7.6 out of 10, Good, (958 reviews)

7.6/10

Good

(958 reviews)

"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."

Edwin

The price is S$116

S$116

includes taxes & fees

10 Nov - 11 Nov

Baymont by Wyndham Easton

A pool area with lounge chairs, a hot tub, and a view of the ocean.

An outdoor patio with brick flooring, wooden pergola, and tables with chairs.

A hotel room with a bed, a desk, a chair, a TV, and a view of the outside.

A hotel with multiple balconies, a swimming pool, and a view of the ocean.

4. Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

2.5 star property

Midtown Ocean City

8.8 out of 10, Excellent, (1,002 reviews)

8.8/10

Excellent

(1,002 reviews)

"Very enjoyable stay. Staff was very warm and welcoming."

Erin

The price is S$84

S$84

includes taxes & fees

3 Dec - 4 Dec

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

A multi-story hotel with a covered entrance and a flagpole.

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

A poolside area with lounge chairs and a mural of a sunset over water.

5. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property

Grasonville

8.0 out of 10, Very good, (1,002 reviews)

8.0/10

Very good

(1,002 reviews)

"Nice location & stay"

Holly

The price is S$128

S$128

includes taxes & fees

15 Nov - 16 Nov

Best Western Kent Narrows Inn

A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.

A multi-story hotel with balconies, a prominent entrance, and a view of the water.

A dining area with a table set for two, potted plants, and a view through large windows.

A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.

6. Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront

3.0 star property

Downtown Ocean City

9.0 out of 10, Wonderful, (1,001 reviews)

9.0/10

Wonderful

(1,001 reviews)

"Very well maintained staff was super nice and professional higher recommend staying here"

Patricia

The price is S$116

S$116

includes taxes & fees

7 Dec - 8 Dec

Cambria Hotel Ocean City - Bayfront

A two-story house with a porch, a front door, and a small garden area.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

7. The Wildset

The Wildset

2.5 star property

Downtown St. Michaels

9.8 out of 10, Exceptional, (526 reviews)

9.8/10

Exceptional

(526 reviews)

"Wonderful place to stay. The staff was beyond helpful. Everything is homemade and nightly s’mores by the fire pit were so much fun! Can not recommend this place enough!"

Dena

The price is S$313

S$313

includes taxes & fees

1 Dec - 2 Dec

The Wildset

A clear pool with palm trees, lounge chairs, and umbrellas.

A beachside bar with Adirondack chairs, a pool, and a view of the ocean.

A round table with breakfast items and drinks, set against a backdrop of a calm sea and clear sky.

A beach resort with a pool, sun loungers, and umbrellas.

8. Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

3.0 star property

Downtown Ocean City

9.4 out of 10, Exceptional, (1,468 reviews)

9.4/10

Exceptional

(1,468 reviews)

"Wonderful stay with great eats."

Christopher

The price is S$129

S$129

includes taxes & fees

6 Dec - 7 Dec

Holiday Inn & Suites Ocean City by IHG

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

9. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 star property

Easton

9.0 out of 10, Wonderful, (1,008 reviews)

9.0/10

Wonderful

(1,008 reviews)

"Plenty of parking! Comfortable beds and pillows. The staff was amazing, kind, helpful and friendly. I would definitely stay there again."

Margaret

The price is S$168

S$168

includes taxes & fees

15 Nov - 16 Nov

Best Western Plus Easton Inn & Suites

A balcony with a view of the sea, a pool, and a row of chairs.

A coastal hotel with a marina, a large building with multiple floors, and a view of the city skyline in the background.

A poolside area with lounge chairs and umbrellas, reflecting the sky and clouds.

A modern bar area with a long counter, multiple bar stools, and ambient lighting.

10. Residence Inn by Marriott Ocean City

Residence Inn by Marriott Ocean City

3.0 star property

Midtown Ocean City

9.0 out of 10, Wonderful, (1,002 reviews)

9.0/10

Wonderful

(1,002 reviews)

"Clean large room-great view, welcoming staff especially during breakfast-delicious options, last minute stay turned out to be great decision"

Karen

The price is S$118

S$118

includes taxes & fees

12 Nov - 13 Nov

Residence Inn by Marriott Ocean City

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Hotels with connecting rooms in Eastern Shore

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Eastern Shore hotels with connecting rooms

1. Holiday Inn Express Annapolis East-Kent Island by IHG

2. Hyatt Regency Chesapeake Bay

3. Baymont by Wyndham Easton

4. Hampton Inn & Suites Ocean City/Bayfront-Convention Center

5. Best Western Kent Narrows Inn

6. Cambria Hotel Ocean City - Bayfront

7. The Wildset

8. Holiday Inn & Suites Ocean City by IHG

9. Best Western Plus Easton Inn & Suites

10. Residence Inn by Marriott Ocean City

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