Winchester Cottages
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Cottages in Winchester
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit MD
$198 nightly
The price is $209 total per night
$209 total
Dec 8 - Dec 9
Total with taxes and fees
This cottage is 1 mi (1.6 km) from Susquehanna River and 5 mi (8 km) from Hollywood Casino.
Air conditioning
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Elkton MD
Located in Elkton, this cottage is on the waterfront, a 5-minute drive from Chesland Park and 6 minutes from Brantwood Park.
Kitchen
Washer
Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit MD
$232 nightly
The price is $246 total per night
$246 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
A stay at this cottage places you in the heart of Port Deposit, a 1-minute drive from Susquehanna River and 6 minutes from Hollywood Casino.
Kitchen
Washer
Charming Carriage House in the Heart of Kennett
Kennett Square PA
$401 nightly
The price is $443 total per night
$443 total
Dec 8 - Dec 9
Total with taxes and fees
With a stay at this cottage in Kennett Square, you'll be within a 10-minute drive of Longwood Gardens and Anson B. Nixon Park.
Washer
Dryer
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Elkton MD
With a stay at this cottage in Elkton, you'll be within a 10-minute drive of Chesland Park and Brantwood Park.
Pool
Kitchen
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Earleville MD
Located in Earleville, this cottage is in a rural location, within a 15-minute drive of Earleville Wildlife Management Area and Earleville Wildlife Management Area.
Kitchen
Washer
Walk to Town & River: Charming Home in North East!
North East MD
Located in North East, this cottage is a 2-minute drive from Upper Bay Museum and 5 minutes from Milburn Stone Theater.
Kitchen
Parking included
Waterfront Cottage on the C&D Canal!
Chesapeake City MD
When you a stay at this cottage in Chesapeake City, you'll be on the waterfront, just steps from The Pell Gardens and Chesapeake Inn Marina.
Kitchen
Free WiFi
Cozy Cottage on the North East River in Town!
North East MD
Located in North East, this cottage is on the waterfront, a 2-minute drive from Upper Bay Museum and 5 minutes from Milburn Stone Theater.
Kitchen
Washer
Charming 2-bedroom water oriented cottage with water access
North East MD
Located in North East, this cottage is on a river, a 4-minute drive from Upper Bay Museum and 9 minutes from Roachs Shore.
Kitchen
Washer
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.
Winchester Cottages essential information
Accommodation | 29 Cottages |
|---|---|
Lowest Price | $209 |
Highest Price | $446 |
Popular accommodation | Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland. , Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC, Quarry Landing - Center of Town & River View - 3 Bedroom, Charming Carriage House in the Heart of Kennett, Chesapeake City Pool Retreat – Waterfront Stay in the Woods, Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Walk to Town & River: Charming Home in North East!, Waterfront Cottage on the C&D Canal!, Cozy Cottage on the North East River in Town!, Charming 2-bedroom water oriented cottage with water access, Spruce Edge Guest House , Thunder Hill Retreat - Spacious/Deck/Hot tub |