A beach with seagulls, a rocky shoreline, and houses in the background.

Guest Houses in Calvert County

Compare and save

  • 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

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

Top Cities in Calvert County

A harbor with boats docked, a pier, and a row of houses along the water.
Guest HousesGuest Houses

Chesapeake Beach

Chesapeake Beach

Our top choices for Calvert County guest houses

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

1. The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (169 reviews)
"The best vacation ever. Location is everything. Just a slice of heaven on earth. We will never top this stay. Tried to book a reservation before we left. Will return as often as possible."
United States
William
The price is CA $263
CA $289 total
includes taxes & fees
Oct 19 - Oct 20
The Tilghman Island Inn
A modern kitchen with a stainless steel refrigerator, white cabinetry, a wooden dining table with chairs, and a large window with blinds.

2. 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, (30 reviews)
"Very clean, nice area and very convenient to where we needed to be "
United States
Jordan B.
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

3. 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 $224
CA $253 total
includes taxes & fees
Oct 15 - Oct 16
Spacious La Plata Escape
A narrow concrete pathway leading to a garage with a stone wall on one side and a wooden fence on the other.

4. Woody Westover at Hillcrest

Woody Westover at Hillcrest
Southeast
9.4 out of 10, Exceptional, (24 reviews)
"Great place to stay in DC if you need the basics. Property was clean, in a very cute neighborhood with driveway parking. It was a 15 minute drive to the National Mall. The host was pleasant, provided clear instructions, and responded quickly."
United States
Daniela
The price is CA $122
CA $319 total
includes taxes & fees
Oct 17 - Oct 18
Woody Westover at Hillcrest
A modern living room with a sofa, dining table, and a TV mounted on the wall.

5. Entire Suite Free Off Street Parking

Entire Suite Free Off Street Parking
Southeast
9.6 out of 10, Exceptional, (14 reviews)
"My family had a great stay in DC. The size and layout worked perfectly for my family. The home is conveniently located, and having a parking spot was awesome. Our hosts were communicative and so kind. We will stay here again on our next visit!"
United States
Teneka S.
Entire Suite Free Off Street Parking
A staircase with alternating black and wooden steps, a red door with a 'Stay Back' sign, and a framed picture collection on the wall.

6. Barefoot Cottage A Quiet Coastal Retreat

Barefoot Cottage A Quiet Coastal Retreat
Arundel on the Bay
10.0 out of 10, Exceptional, (3 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.
Barefoot Cottage A Quiet Coastal Retreat
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Calvert County Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Clean room. Great breakfast."
Eric 2-night trip
Posted 5 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Calvert County

Calvert County Guest Houses information

Number of reviews
75
Accommodation
7 Guest Houses
Lowest Price
CA $253
Highest Price
CA $319

Explore a world of travel with Expedia