Guest Houses in Caroline County
Maryland
United States of America
Guest Houses
Expedia.ca

Caroline County Travel Guide Caroline County Hotels Caroline County Flights Car Rentals in Caroline County Caroline County Vacations Vacation Rentals in Caroline County

A river with a green embankment and a boat.

Guest Houses in Caroline County

Compare and save

Where to?

Dates

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

November 2026

SunSunday

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

December 2026

SunSunday

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

Travellers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Top cities in Caroline County

A sunset over a lake with a forest in the background.

Denton

Federalsburg

A straight road flanked by trees and grass fields.

Ridgely

Preston

Greensboro

Marydel

Henderson

Goldsboro

Tanyard

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Caroline County guest houses

A large building with a swimming pool, dock, and green surroundings.

An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

A spacious indoor dining area with large windows, tables, and chairs.

A modern lounge area with a fireplace, seating, and a view of the outdoors.

1. The Tilghman Island Inn

The Tilghman Island Inn

3.5 star property

Tilghman

9.4 out of 10, Exceptional, (172 reviews)

9.4/10

Exceptional

(172 reviews)

"X"

Kelly

The Tilghman Island Inn

2. Room-bright & Cozy Room Peaceful Dover S

Room-bright & Cozy Room Peaceful Dover S

2.5 star property

Dover

6.0 out of 10, (1 review)

6.0/10

(1 review)

Room-bright & Cozy Room Peaceful Dover S

A bedroom with a large bed, a red dresser, a bicycle, and various wall art.

A hot tub with a marble design, surrounded by a wooden deck and a covered area with string lights.

A circular outdoor seating area with a round table and benches, surrounded by a wooden deck and a blue canopy.

A wooden outdoor shower with a white curtain, a towel hanging on a hook, and a small shelf with bottles.

3. Room-red Room DE With Spa Access

Room-red Room DE With Spa Access

2.0 star property

Dover

Room-red Room DE With Spa Access

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.

View all properties

Top reviews in Caroline County

A poolside area with lounge chairs, a potted plant, and a view of the pool.

A modern hotel room with a shower, a bed, a desk, and a large window offering a view of the outdoors.

A breakfast bar with a variety of fruits, a waffle station, and a bakery section.

A hotel lobby with a modern design, featuring a patterned carpet, seating areas, a snack bar, and a refrigerator.

Hampton Inn Milford

Milford

10/10 Excellent

The hotel is pretty good, clean, good parking and good breakfast. It is located in a very quiet area off Hwy 1, with access through a back road. It is however away from restaurants and shops, which makes a bit inconvenient.

Laura

Reviewed August 27, 2022Reviewed August 27, 2022

Hampton Inn Milford

A modern lobby with a large sofa, seating area, and a television.

A modern microhotel with a swimming pool, outdoor seating, and a parking area.

A Microtel hotel with a modern design, featuring multiple floors and a covered entrance area.

Microtel Inn & Suites by Wyndham Milford

Milford

10/10 Excellent

Nous avons apprécié notre expérience. Le personnel était très agréable et a répondu à toutes nos questions.

Sylvain

Reviewed August 9, 2026Reviewed August 9, 2026

Microtel Inn & Suites by Wyndham Milford

A multi-story hotel with a symmetrical facade, large windows, and a central entrance with a welcoming archway.

A vending machine stocked with beverages and snacks, a refrigerator with food items, and shelves with packaged goods.

A modern kitchen area with a yellow brick wall, stainless steel appliances, and a seating area with tables and chairs.

A hotel room with a large bed, a desk, a window with yellow curtains, and a view of the outside.

Microtel Inn & Suites by Wyndham Dover

Dover

10/10 Excellent

Front desk staff was wonderful. And, your vending prices are ridiculously lower - thanks.

Elaine

Reviewed July 30, 2023Reviewed July 30, 2023

Microtel Inn & Suites by Wyndham Dover

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

An outdoor event area with round tables and a view of the water.

Hyatt Place Kent Narrows & Marina

Grasonville

10/10 Excellent

Good place

Uri

Reviewed July 11, 2026Reviewed July 11, 2026

Hyatt Place Kent Narrows & Marina

A spacious lobby with a central fountain, marble flooring, and columns with greenery.

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

Bally's Dover Casino Resort

Dover

10/10 Excellent

The staff are extremely helpful and informative and friendly.

Howard

Reviewed August 31, 2026Reviewed August 31, 2026

Bally's Dover Casino Resort

An indoor swimming pool with clear views through large windows, wooden ceiling beams, and a seating area with tables and chairs.

A hotel lobby with a wooden staircase, a reception desk, and a second-floor balcony.

A hotel room with a large bed, a separate bathroom with a bathtub, a television, and a lamp.

A hotel room with a reception desk, a sofa, two lamps, a framed picture on the wall, and a patterned carpet.

Quality Inn & Suites Harrington - Milford

Harrington

10/10 Excellent

Wonderful. Great staff. Great place and soooo dam nice.

SANDRA

Reviewed July 30, 2023Reviewed July 30, 2023

Quality Inn & Suites Harrington - Milford

A hotel lobby with a fireplace, seating area, and a television.

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 hotel room with a bed, a sofa, a dining table, and a small round table.

Comfort Inn & Suites Chestertown

Chestertown

10/10 Excellent

Bon service

Sébastien

Reviewed August 22, 2026Reviewed August 22, 2026

Comfort Inn & Suites Chestertown

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

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

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

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

Holiday Inn Express Hotel & Suites Dover by IHG

Dover

10/10 Excellent

We stay here every year and love it. Rooms are really spacious and clean.

Hoang Tram

Reviewed September 24, 2025Reviewed September 24, 2025

Holiday Inn Express Hotel & Suites Dover by IHG

A spacious hotel lobby with multiple dining tables, comfortable seating, a large TV screen, and modern lighting fixtures.

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.

Hilton Garden Inn Dover

Dover

10/10 Excellent

Excellent

Denene

Reviewed May 20, 2019Reviewed May 20, 2019

Hilton Garden Inn Dover

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.

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

This was a great place to stay! Very clean and friendly staff!

justin

Reviewed May 12, 2026Reviewed May 12, 2026

Best Western Plus Easton Inn & Suites

An indoor swimming pool with lounge chairs and a no diving sign.

A buffet with various food items in metal containers, a coffee station, and a sign indicating a vegetarian omelet option.

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

Holiday Inn Express Easton by IHG

Easton

10/10 Excellent

Clean room excellent breakfast and excellent front desk

Vito

Reviewed August 14, 2022Reviewed August 14, 2022

Holiday Inn Express Easton by IHG

A modern breakfast area with a counter, seating, and a chalkboard menu.

A modern dining area with a large table, chairs, and pendant lighting.

An indoor swimming pool with clear glass ceilings, blue walls, and wooden lounge chairs.

A modern reception area with a wooden reception desk, red seating, and a "Welcome to the Blue Hen State" sign.

Hampton Inn Seaford

Seaford

10/10 Excellent

Everything was good.

Jean-François

Reviewed October 2, 2025Reviewed October 2, 2025

Hampton Inn Seaford

Explore a world of travel with Expedia

Lodging
Flights
Packages
Cars
Things to do

Queenstown Waterfront
Standard Link for Queenstown Waterfront
Cabin Rentals in Goldsboro
Standard Link for Cabin Rentals in Goldsboro
Apartments in Oxford
Standard Link for Apartments in Oxford
Hyatt Hotels in St. Michaels
Standard Link for Hyatt Hotels in St. Michaels
Houseboats in Queenstown
Standard Link for Houseboats in Queenstown
Preston Hotels
Standard Link for Preston Hotels
Casino Hotels in Cambridge
Standard Link for Casino Hotels in Cambridge
Cass
Standard Link for Cass
Marriott Hotels & Resorts in St. Michaels
Standard Link for Marriott Hotels & Resorts in St. Michaels
Cottages in Tilghman
Standard Link for Cottages in Tilghman
Lodges in Woolford
Standard Link for Lodges in Woolford
Cabin Rentals in Federalsburg
Standard Link for Cabin Rentals in Federalsburg
Cottages in Linkwood
Standard Link for Cottages in Linkwood
Cottages in Betterton
Standard Link for Cottages in Betterton
B&B in Woolford
Standard Link for B&B in Woolford
Baltimore Hotels
Standard Link for Baltimore Hotels
B&B in Gibson Island
Standard Link for B&B in Gibson Island
Cabin Rentals in Newcomb
Standard Link for Cabin Rentals in Newcomb
Oxford Hotels
Standard Link for Oxford Hotels
4 Star Hotels in Algonquin
Standard Link for 4 Star Hotels in Algonquin
Easton Hotels
Standard Link for Easton Hotels
New! Gorgeous Waterfront Estate with Saltwater pool
Standard Link for New! Gorgeous Waterfront Estate with Saltwater pool
Centreville Hotels
Standard Link for Centreville Hotels
Cabin Rentals in Maryland
Standard Link for Cabin Rentals in Maryland
B&B in Preston
Standard Link for B&B in Preston
Vacation Homes in Pomona
Standard Link for Vacation Homes in Pomona
Marriott Hotels & Resorts in Cambridge
Standard Link for Marriott Hotels & Resorts in Cambridge
Cabin Rentals in Eastern Shore
Standard Link for Cabin Rentals in Eastern Shore
Walk to Park & River
Standard Link for Walk to Park & River
Minutes from Downtown St. Michaels
Standard Link for Minutes from Downtown St. Michaels
Cambridge Hotels
Standard Link for Cambridge Hotels
Downtown Cambridge Hotels
Standard Link for Downtown Cambridge Hotels
Family Retreat at Lansdowne Manor
Standard Link for Family Retreat at Lansdowne Manor
Luxury Hotels in Cambridge
Standard Link for Luxury Hotels in Cambridge
Hotels with an Indoor Pool in Kent Narrows
Standard Link for Hotels with an Indoor Pool in Kent Narrows
Denton Hotels
Standard Link for Denton Hotels
5 Star Hotels in Secretary
Standard Link for 5 Star Hotels in Secretary
B&B in Royal Oak
Standard Link for B&B in Royal Oak
Queenstown Hotels
Standard Link for Queenstown Hotels
Pet-Friendly Hotels in Cambridge
Standard Link for Pet-Friendly Hotels in Cambridge
Wades Point Inn
Standard Link for Wades Point Inn
Hotels with Waterslides in Downtown Cambridge
Standard Link for Hotels with Waterslides in Downtown Cambridge
Motels in Eastern Shore
Standard Link for Motels in Eastern Shore
Cottages in Maryland
Standard Link for Cottages in Maryland
Vacation Homes in Kent Island
Standard Link for Vacation Homes in Kent Island
Cottages in Gibson Island
Standard Link for Cottages in Gibson Island
Hotels with Waterslides in Cambridge
Standard Link for Hotels with Waterslides in Cambridge
Ironman & Eagleman
Standard Link for Ironman & Eagleman
Chalets in Centreville
Standard Link for Chalets in Centreville
Motels in Maryland
Standard Link for Motels in Maryland
Motels in Royal Oak
Standard Link for Motels in Royal Oak
Spacious 7
Standard Link for Spacious 7
Robert Morris Inn
Standard Link for Robert Morris Inn
Minutes from Downtown St. Michaels
Standard Link for Minutes from Downtown St. Michaels
B&B in Maryland
Standard Link for B&B in Maryland
Rv Parks in Kennedyville
Standard Link for Rv Parks in Kennedyville
Grasonville Hotels
Standard Link for Grasonville Hotels
St. Michaels Hotels
Standard Link for St. Michaels Hotels
Hotels near Avalon Theatre
Standard Link for Hotels near Avalon Theatre
Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"
Standard Link for Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"
Apartments in Maryland
Standard Link for Apartments in Maryland
Kent Island Resort
Standard Link for Kent Island Resort
Oceanfront Hotels in Eastern Shore
Standard Link for Oceanfront Hotels in Eastern Shore
Villas in Georgetown
Standard Link for Villas in Georgetown
Cabin Rentals in Woolford
Standard Link for Cabin Rentals in Woolford
The Colonial Farmhouse with Private Boat Rental
Standard Link for The Colonial Farmhouse with Private Boat Rental
Ridgely Hotels
Standard Link for Ridgely Hotels
Motels in Secretary
Standard Link for Motels in Secretary
Adults Only Resorts & in Eastern Shore
Standard Link for Adults Only Resorts & in Eastern Shore
Hilton Hotels in Eastern Shore
Standard Link for Hilton Hotels in Eastern Shore
Farmstay in Georgetown
Standard Link for Farmstay in Georgetown

Flights to Cambridge
Standard Link for Flights to Cambridge
Flights from Vancouver (YVR) to Baltimore (BWI)
Standard Link for Flights from Vancouver (YVR) to Baltimore (BWI)
Flights from Toronto (YYZ) to Baltimore (BWI)
Standard Link for Flights from Toronto (YYZ) to Baltimore (BWI)
Flights from Preston
Standard Link for Flights from Preston
Flights to St. Michaels
Standard Link for Flights to St. Michaels
Flights from Buffalo (BUF) to Baltimore (BWI)
Standard Link for Flights from Buffalo (BUF) to Baltimore (BWI)
Flights to Eastern Shore
Standard Link for Flights to Eastern Shore
Flights from Allentown (ABE) to Easton (ESN)
Standard Link for Flights from Allentown (ABE) to Easton (ESN)
Flights from Calgary (YYC) to Baltimore (BWI)
Standard Link for Flights from Calgary (YYC) to Baltimore (BWI)
Flights from Montreal (YUL) to Cambridge (CGE)
Standard Link for Flights from Montreal (YUL) to Cambridge (CGE)
Flights from Winnipeg (YWG) to Baltimore (BWI)
Standard Link for Flights from Winnipeg (YWG) to Baltimore (BWI)
Flights from Washington (DCA) to Easton (ESN)
Standard Link for Flights from Washington (DCA) to Easton (ESN)
Flights from Cincinnati (CVG) to Easton (ESN)
Standard Link for Flights from Cincinnati (CVG) to Easton (ESN)
Flights from Toronto (YYZ) to Cambridge (CGE)
Standard Link for Flights from Toronto (YYZ) to Cambridge (CGE)
Flights to Baltimore
Standard Link for Flights to Baltimore
Flights from Church Hill
Standard Link for Flights from Church Hill
Flights from Los Angeles (LAX) to Easton (ESN)
Standard Link for Flights from Los Angeles (LAX) to Easton (ESN)
Flights to Maryland
Standard Link for Flights to Maryland

Visit Maryland
Standard Link for Visit Maryland
Visit Cambridge
Standard Link for Visit Cambridge
Visit Easton
Standard Link for Visit Easton
Long Wharf Park
Standard Link for Long Wharf Park
Visit Eastern Shore
Standard Link for Visit Eastern Shore
Visit Downtown Cambridge
Standard Link for Visit Downtown Cambridge

Avis Rental Cars in Easton
Standard Link for Avis Rental Cars in Easton
Rent A Wreck Rental Cars in Eastern Shore
Standard Link for Rent A Wreck Rental Cars in Eastern Shore

Things to do in Maryland
Standard Link for Things to do in Maryland

Guest Houses in Caroline County

Change your mind

Treat yourself

Be picky

Top cities in Caroline County

Denton

Check prices for these dates

Our top choices for Caroline County guest houses

1. The Tilghman Island Inn

2. Room-bright & Cozy Room Peaceful Dover S

3. Room-red Room DE With Spa Access

Top reviews in Caroline County

Hampton Inn Milford

10/10 Excellent

Explore a world of travel with Expedia