Search Guest Houses in Eastern Shore from CA $159

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Eastern Shore guest houses

A modern kitchen with a stainless steel refrigerator, white cabinetry, a wooden dining table with chairs, and a large window with blinds.

1. 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.
The price is CA $160
CA $485 total
includes taxes & fees
Nov 9 - Nov 10
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
A dining area with brick flooring, white chairs, a wooden table, and a chandelier.

2. Palmer House King | Vaulted Ceilings & Deck

Palmer House King | Vaulted Ceilings & Deck
South Rehoboth
10.0 out of 10, Exceptional, (4 reviews)
"Location was excellent. The room was clean and as described. Great for a quick getaway weekend!"
United States
David C.
The price is CA $233
CA $278 total
includes taxes & fees
Nov 18 - Nov 19
Palmer House King | Vaulted Ceilings & Deck
Interior

3. Farmette Guesthouse|Fire pit|Private|Creekside

Farmette Guesthouse|Fire pit|Private|Creekside
New Providence
9.8 out of 10, Exceptional, (10 reviews)
"Clean, quiet and comfortable. Good communication with the host. We enjoyed our stay."
United States
Christine O.
The price is CA $179
CA $369 total
includes taxes & fees
Nov 16 - Nov 17
Farmette Guesthouse|Fire pit|Private|Creekside
A stone building with a wooden door, a window with a wreath, and a bell above the door.

4. Ironmaster Mansion — 1700's historic stone guest house with creek view

Ironmaster Mansion — 1700's historic stone guest house with creek view
Pequea
10.0 out of 10, Exceptional, (28 reviews)
"This historical property has been meticulously updated with modern conveniences and decorated in a charming and tasteful cottage style. The host was very positive and communicative and provided lovely fresh flowers and locally made sweet treats and an outstanding locally made chicken pot pie that were very much appreciated following a late arrival!"
United States
Deborah W.
The price is CA $384
CA $630 total
includes taxes & fees
Nov 14 - Nov 15
Ironmaster Mansion — 1700's historic stone guest house with creek view
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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Learn more about Eastern Shore

Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savour fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants.

See all hotels in Eastern Shore
A historic white mansion with a sign in front.

Top reviews in Eastern Shore

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

The Wildset

The Wildset
Downtown St. Michaels

10/10 Excellent

Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Canada
Mairi
Reviewed August 11, 2026
The Wildset

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