10 Results
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

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

Chesapeake Bay Ski Vacation Rentals(10)

10 Results
  • 12 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 40
2 - 7 night min stay
(11)
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 20
3 night min stay
(7)
$257 - $400
per night
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night min stay
(35)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 7 night min stay
(13)
  • 2 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 6
3 night min stay
(4)
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night min stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night min stay
(15)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night min stay
(19)
  • 3 BR,
  • 3 BA,
  • Sleeps 12
3 night min stay
(23)
$275 - $300
per night
3 - 6 night min stay
  • Studio,
  • 2 BA,
  • Sleeps 6
3 - 6 night min stay
 

Recent Chesapeake Bay Reviews

Perfect cottage for a girls weekend

5 of 5
Harbor Hideaway was the PERFECT cottage for our girls getaway. This was our first time to St. Michaels, and we're already planning next years trip (and stay in Harbor Hideaway, of course). The cottage had everything we needed, and we really appreciated all of the owner's little touches to make it feel like home. Everything was so clean and cozy! The location is perfect, too - we walked to all of the shops and restaurants in town. There was snow on the ground so we didn't get to appreciate the backyard, but it looked perfect and spacious. And, I can't say enough about how easy it was to work with Carol, the owner. I'd definitely recommend this place to anyone! Can't wait until next year!
  • Submitted: Mar 10, 2015
  • Stayed: Mar 2015

Beautiful waterfront with great amenities!

5 of 5
This property is gorgeous; right on the Chesapeake Bay with a beautiful deck to watch the sunrise/sunset from. The pool is well maintained with comfortable patio furniture and the hot tub provides a place to relax and unwind at the end of the day. Our dogs loved playing in the bay from the dock. The neighbors were wonderful and very friendly; however we only saw them once so it was a nice respite away from the rest of the world. We highly recommend this rental; it's everything they describe it to be and more!
  • Submitted: Feb 21, 2015
  • 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