A historic downtown street at dusk with vintage street lamps, brick buildings, and a sign for 'FELSH POINT'.

Guest Houses in Maryland

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Top Cities in Maryland

A capitol building with a dome, surrounded by autumn foliage.
Guest HousesGuest Houses

Washington

Washington

Our top choices for Maryland guest houses

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

1. The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (163 reviews)
"Love the Inn! Awesome self contained little resort escape destination Been there over the years! No restaurants or bar in operation at the facility now and St Michaels is a 15 mile ride!!! Unfortunate for future willingness to visit!"
United States
Robert M
The price is CA $261
CA $287 total
includes taxes & fees
Sep 28 - Sep 29
The Tilghman Island Inn
A street lined with multi-story buildings, parked cars, and a sidewalk with fallen leaves.

2. Amazing Townhouse-Heart of Little Italy

Amazing Townhouse-Heart of Little Italy
2.0 star property
Little Italy
8.6 out of 10, Excellent, (8 reviews)
"A very peaceful, charming, and comfortable alternative to a conference hotel, and only a 5 minute walk!"
United States
Lynette
Amazing Townhouse-Heart of Little Italy
A balcony with two white cushioned chairs and a small table, a yellow textured wall, and a red-roofed building in the background.

3. Eden Park Guest House

Eden Park Guest House
3.5 star property
Takoma Park
7.8 out of 10, Good, (167 reviews)
"Excellent location."
United States
Morgan
The price is CA $130
CA $171 total
includes taxes & fees
Oct 26 - Oct 27
Eden Park Guest House
A modern kitchen with a stainless steel refrigerator, white cabinetry, a wooden dining table with chairs, and a large window with blinds.

4. West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Homewood
10.0 out of 10, Exceptional, (29 reviews)
"Very clean, nice area and very convenient to where we needed to be "
United States
Jordan B.
The price is CA $206
CA $537 total
includes taxes & fees
Sep 28 - Sep 29
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
A bedroom with a bed, a dresser, a chair, a window with curtains, and a wall with a picture.

5. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is CA $212
CA $472 total
includes taxes & fees
Sep 27 - Sep 28
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
An indoor swimming pool with multiple lanes, a lifeguard chair, and a clock on the wall.

6. The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View!

The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View!
Accident
9.6 out of 10, Exceptional, (87 reviews)
"Great place to stay and great host !"
United States
Rachelle O.
The price is CA $121
CA $336 total
includes taxes & fees
Sep 29 - Sep 30
The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View!
A brick fireplace with two built-in shelves and a mantel, flanked by wooden chairs.

7. Inn at Springfield Manor

Inn at Springfield Manor
3.0 star property
Thurmont
8.6 out of 10, Excellent, (64 reviews)
"LOVELY place, lovely people"
United States
Thomas
The price is CA $282
CA $299 total
includes taxes & fees
Sep 26 - Sep 27
Inn at Springfield Manor
A modern kitchen with white cabinetry, a central island, and a dining area with a wooden table and chairs.

8. French Farm house /Apartment.

French Farm house /Apartment.
Beallsville
9.8 out of 10, Exceptional, (7 reviews)
"It was a great place to stay.Will definitely be back sometime "
United States
Jorge M.
French Farm house /Apartment.
A swimming pool with a tiled deck, a covered patio area, and a large house with a balcony.

9. Island Life! Kent Island Waterfront with Pool-Bring your boat!

Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville
10.0 out of 10, Exceptional, (217 reviews)
"My Family and I had a wonderful Stay. The place was clean, the host were Great. We caught a bunch of crabs off the Dock, the kids enjoyed the pool and Kayaks. We plan on booking the house in the Future."
United States
Tomas D.
Island Life! Kent Island Waterfront with Pool-Bring your boat!
A garden with raised beds and a greenhouse structure.

10. INDULGE - FRESH FLOWERS, MANY AMENITIES

INDULGE - FRESH FLOWERS, MANY AMENITIES
Middletown
10.0 out of 10, Exceptional, (56 reviews)
"Great place to stay in rural Maryland and have all you need. Awesome place!"
United States
Thomas C.
The price is CA $148
CA $272 total
includes taxes & fees
Oct 18 - Oct 19
INDULGE - FRESH FLOWERS, MANY AMENITIES
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

11. Spacious La Plata Escape

Spacious La Plata Escape
2.0 star property
La Plata
8.6 out of 10, Excellent, (4 reviews)
"Great stay. The hosts were very communicative and answered all questions. Everything was nicer in person and smelled really good. I have no complaints and would stay again"
United States
Jazelle
The price is CA $211
CA $238 total
includes taxes & fees
Sep 28 - Sep 29
Spacious La Plata Escape
A cozy living room with a fireplace, a television, and a chandelier.

12. Butterfly Suite-Enchanted Elegance near DCL/Wisp! Fireplace! Meadow/Forest View!

Butterfly Suite-Enchanted Elegance near DCL/Wisp! Fireplace! Meadow/Forest View!
Accident
10.0 out of 10, Exceptional, (95 reviews)
"It was nice!"
United States
Anne R.
The price is CA $121
CA $291 total
includes taxes & fees
Sep 29 - Sep 30
Butterfly Suite-Enchanted Elegance near DCL/Wisp! Fireplace! Meadow/Forest View!
A room with a large plant in a square planter, a bookshelf filled with books, a television, and a window with a view of greenery.

13. Private two story guesthouse in Takoma Park

Private two story guesthouse in Takoma Park
Takoma Park
9.0 out of 10, Wonderful, (12 reviews)
"Cute place, comfy, free street parking. Come and go as you please. I would stay again. Thx to the hosts!"
United States
SnowDust
Private two story guesthouse in Takoma Park
A staircase with alternating black and wooden steps, a red door with a 'Stay Back' sign, and a framed picture collection on the wall.

14. Barefoot Cottage A Quiet Coastal Retreat

Barefoot Cottage A Quiet Coastal Retreat
Arundel on the Bay
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay here. It was perfect for our trip and in a great location. I have no complaints and would stay here again if we visited this area!"
United States
Kristin H.
The price is CA $200
CA $261 total
includes taxes & fees
Sep 28 - Sep 29
Barefoot Cottage A Quiet Coastal Retreat
A living room with a fireplace, leather sofa, and a rug.

15. Akeem's guest house

Akeem's guest house
2.0 star property
Silver Spring
Akeem's guest house

16. Room in Guest Room - Twin Bunk-style Bedroom Close to Downtown

Room in Guest Room - Twin Bunk-style Bedroom Close to Downtown
2.0 star property
Midtown-Edmondson
2.0 out of 10, (1 review)
"This property appears to be in an area that is dangerous. None of the pictures really show it but it's really alarming. Mostly what appears dangerous is the surrounding area."
United States
Kenneth
Room in Guest Room - Twin Bunk-style Bedroom Close to Downtown

17. Second Floor East Standard Deluxe

Second Floor East Standard Deluxe
2.0 star property
North East
Second Floor East Standard Deluxe

18. Top Floor Family Deluxe Bay View

Top Floor Family Deluxe Bay View
2.0 star property
North East
Top Floor Family Deluxe Bay View

19. Room in Guest Room - Cozy Bedroom Close to Downtown

Room in Guest Room - Cozy Bedroom Close to Downtown
2.0 star property
Midtown-Edmondson
Room in Guest Room - Cozy Bedroom Close to Downtown

20. Center Parlor Room at Sandy Cove

Center Parlor Room at Sandy Cove
2.5 star property
North East
Center Parlor Room at Sandy Cove
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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Top Maryland Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I liked the staff!"
Elliott 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Maryland

Maryland Guest Houses information

Number of reviews
563
Accommodation
44 Guest Houses
Lowest Price
CA $171
Highest Price
CA $537

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