Top Country Houses in Dorchester County in 2026

A lighthouse on a pier with a red roof and white walls, surrounded by calm water.

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Our top choices for Dorchester County country houses

Waterfront 4-bedroom homestead with pool, jacuzzi, and dock access. Sleeps 11!

Heathsville

"Our stay at the homestead was so relaxing! We had amazing water views from the home, nice afternoon walks and soaks in the hot tub, and we thoroughly enjoyed the spacious kitchen and screened in porch. Our beds were firm and comfortable, and evenings were so peaceful due to its location off the main road. We were close to several cute towns that we were able to explore during the day. We definitely want to come back here when the weather is warmer to enjoy all the warm weather amenities."

Kayla F.

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Fishing Creek

melissa w.

Home of the Terrapin King

Crisfield

Jamie B.

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Denton

Dallas S.

Multi-home Waterfront Eastern Shore Retreat with 80+ acres to yourself

Cambridge

Anonymous traveler

The 1934 Farmhouse - close to the beaches

Georgetown

Jessica

AED 1,056 total

includes taxes & fees

27 Jul - 28 Jul

On the beach, sun loungers, beach towels

Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier

Cambridge

Richard S.

Modern Farmhouse: 12.5 Acres & 2 Fire Pits

Lothian

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Top Dorchester County Hotel Reviews

Quality Inn & Suites Georgetown - Seaford

8/10 Good

"Good hotel our only issues were the cleaning staff didn’t refresh our room so we had to ask for clean towels and had trash and dirty towels for the two nights we stayed. Other than that it was a good place to stay. Our neighbor was blasting the tv and someone in the room above us was moving furniture at almost midnight and the front desk staff took care of that pretty quickly."

Hyatt Regency Chesapeake Bay

10/10 Excellent

"We love this hotel. the rooms are very comfy and super clean. The infinity pool and other amenities make this a great place to stay if you don't want to leave the resort. My one suggestion is better training for your servers. Most who helped us were super nice, but one or 2 seemed bothered that they needed to wait on us since we were eating around 9 pm. Also, there was one worker in the gift/ coffee shop who was not very friendly any of the times we visited. Normally, in high end resorts everyone is very welcoming."

Days Inn & Suites by Wyndham Seaford

10/10 Excellent

"Stayed in a few "Days Inn" all over the US. This one was best for this chain... This room/bathroom nicer than I expected for the price I got and comparing to other stays locally. Quiet, clean, well appointed, super friendly/helpful staff. -- Somewhat negative: Unless you like waffles or a big carb load in the AM, the breakfast was weak. No eggs, meat, or fresh fruit, and no yogurt. Bagel and cream cheese was fine. Orange Juice was superior. Most importantly, the coffee was good. -- The 2 nights before we stayed at another hotel across the street and the coffee was like mud so my wife had to waste money at Starbucks (also across the way) but this place has good coffee (and also Keurig in the room if into plastic waste). -- LOCATION excellent with Super Walmart, gas stations, fast food, diner, mexican food, Applebee's, Texas Roadhouse Steaks, etc all within about 2 miles, some just a couple hundred yards."