Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Cottages
Estates
Homes
Apartments
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Condos
Farmhouses
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chesapeake Bay Ski Vacation Rentals(8)

8 Results
$250 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(34)
$350 - $550
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 3 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 6
3 night minimum stay
(4)
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(13)
  • 3 BR,
  • 3 BA,
  • Sleeps 12
3 night minimum stay
(21)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night minimum stay
(18)
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 20
3 night minimum stay
(7)
 

Recent Chesapeake Bay Reviews

Sisters Weekend

5 of 5
Wonderful weekend, beautiful weather, terrific sail on the Selina, shopping, Gina's Cafe for incredible tacos, and let's not forget Tilghman Island Day with music, food and working boat races!! Harbor Hideaway and St. Michaels is a special jewel on the eastern shore. Our spring visit and return in October exceeded our expectations!
  • Submitted: Oct 25, 2014
  • Stayed: Oct 2014

Gorgeous Property, but Amenities need attention

4 of 5
This property is absolutely beautiful...park like setting, lots of land, beautiful waterview and spectacular sunrises. The house was comfortable...linens very clean as well as bathrooms. A few things need attention....the grill outside was unusable as the grates were covered in rust and caked on food. Also no propane. Notified the rental agent and though they tried to get new grates, they could not. But they did scrape them down a bit. Also, the A/C in the living room kept shorting out. The ceiling fan in the hot tub room did not work. I would also suggest that some things be checked between tenants...old food left in the refrigerator and dirty laundry in the washing machine. Plus ants are a definite problem. But we enjoyed the solitude and serenity as well as being so close to St. Michaels. We also appreciated how well the grounds were maintained and how clean the pool was.
  • Submitted: Sep 30, 2014
  • Stayed: Sep 2014

tranquility at its finest

5 of 5
no complaints! walking distance to everything clean and very friendly community community private beach and peer clean short drive to clean dog friendly beach peaceful, relaxing home atmosphere would absolutely stay there again
  • Submitted: Jul 30, 2014
  • Stayed: Jul 2014