CyberRentals is part of HomeAway.com, the world's leading vacation rentals marketplace. Search over 170,000 vacation rentals properties now! Click here to see more Chesapeake Bay Vacation Rentals
Vacation Rentals in Chesapeake Bay
| Sort by: | Show rentals per page |
SPECIAL OFFER!
$500 Fall Weekend Getaway special!!!
October 28
-
December 21
Chesapeake Bay Vacation Rental, quiet, beachy, open, bay view – Property 119031
- Chesapeake Bay rental - house, 4 bedrooms, sleeps 12, 2 bathrooms, 1 half bath, beach, near the ocean, balcony
- $1,200 - $1,500/week
- Calendar Last Updated On: Nov 8, 2009
'Jeff's Bed & Fix Your Own Breakfast' Recently back on the rental market, this 3 bedroom with kids quarters is located in the private waterfront community of Long...
One level family vacation home with pool, dock, sheltered cove and lots of living spaces! – Property 7004789
- Chesapeake Bay rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, dock boatslip, DVD
- $2,448 - $5,568/week
- Calendar Last Updated On: Nov 8, 2009
This wonderful family friendly property lies between St. Michaels and Easton on four private park-like acres, with an expansive 4 bedroom home.
Blue Gates – Property 7004792
- Chesapeake Bay rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, dock boatslip, DVD
- $3,712 - $4,912/week
- Calendar Last Updated On: Nov 6, 2009
Elegantly furnished and located in a prestigious estate area of Talbot County, Blue Gates offers a chance to experience the best in Eastern Shore Living.
Expansive 5BR home with great wide water views, pool, beautifully decorated – Property 7004818
- Chesapeake Bay rental - house, 5 bedrooms, sleeps 10, 3 bathrooms, dock boatslip, DVD
- $2,873 - $6,462/week
- Calendar Last Updated On: Nov 6, 2009
Cheerfully decorated and water views from almost every room, this sprawling mostly one level home is a great family spot for those looking to hunker down and cherish...
Nautical Cottage just outside St. Michaels, great getaway spot – Property 7007433
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 6, 3 bathrooms, dock boatslip, DVD
- $1,551 - $2,676/week
- Calendar Last Updated On: Nov 8, 2009
Just a few miles from the historic town of St. Michaels, this adorable nautical cottage is perfect for mini getaway. A private setting welcomes you to your weekend...
Budget friendly home outside St. Michaels – Property 7007434
- Chesapeake Bay rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, dock boatslip, DVD
- $1,513 - $3,385/week
- Calendar Last Updated On: Nov 8, 2009
Barth's Cottage is for families looking to get away but not break the budget. This 3BR one level waterfront home has a lot to offer--pool, private dock (water is...
Close to town with country amenities! Waterfront cottage close to town, perfect for visiting relati – Property 7007437
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 6, 2 bathrooms, dock boatslip, DVD
- $1,186 - $2,286/week
- Calendar Last Updated On: Nov 8, 2009
A newly installed pool for summer 2009 makes this Easton bungalow even better than before! Private dock, newly furnished, gourmet kitchen and just minutes to...
Tilghman Island getaway with private dock, great views, and more! – Property 7007436
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 6, 2 bathrooms, dock boatslip, DVD
- $1,170 - $1,570/week
- Calendar Last Updated On: Nov 8, 2009
This charming cottage is the ideal place for a couple or small group looking for respite and relaxation. On the outskirts of Tilghman Island, come to Choptank...
Contemporary Cottage with pool, tranquil views and great nature watching! – Property 7014511
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 8, 2 bathrooms, dock boatslip, DVD
- $1,646 - $3,336/week
- Calendar Last Updated On: Nov 8, 2009
This waterfront cottage has great cove views of Soltitude Creek, aptly named for the peace and serenity it delivers. Great waterviews with glass doors virtually...
Conveniently located home between Easton and St. Michaels, private with Tred Avon views! – Property 7015502
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 6, 2 bathrooms, dock boatslip, DVD
- $1,375 - $2,275/week
- Calendar Last Updated On: Nov 8, 2009
A restful spot overlooking the Tred Avon River, between Easton and St. Michaels. A great central location find if you are coming into the area for one of the local...
Tilghman Island Cottage with pool, dock, hot tub and wide views! – Property 7018649
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 7, 3 bathrooms, dock boatslip, DVD
- $1,353 - $2,758/week
- Calendar Last Updated On: Nov 8, 2009
A great little cottage with big amenities, Clearview is the answer to your getaway needs. Swimming pool, hot tub, fresh decorating and painting, and views that go...
Cottage with pool, hot tub and great water – Property 7018652
- Chesapeake Bay rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, dock boatslip, DVD
- $1,704 - $3,576/week
- Calendar Last Updated On: Nov 8, 2009
This charming cottage has a great location, just minutes to St. Michaels or Easton, and offers much in the way of family entertainment--pool, hot tub, private dock...
Waterfront Cottage minutes to St. Michaels, hot tub – Property 7018650
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 5, 2 bathrooms, DVD, fireplace
- $1,358 - $2,158/week
- Calendar Last Updated On: Nov 8, 2009
Away from it all! Secluded spot for rest and relaxation, pool, dock, great kayaking! – Property 7022554
- Chesapeake Bay rental - cottage, 3 bedrooms, sleeps 6, 2 bathrooms, dock boatslip, DVD
- $1,291 - $2,696/week
- Calendar Last Updated On: Nov 6, 2009
This unassuming little cottage, tucked in the village of Neavitt, is an oasis unto itself. Private and restful, with private pool, kayaks, and a dock for fishing...
Fantastic restored barn with expansive waterviews, pool, deep water dock – Property 7022553
- Chesapeake Bay rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, dock boatslip, DVD
- $4,149 - $5,649/week
- Calendar Last Updated On: Nov 6, 2009
The view stretching to Oxford from this wonderful restored barn is what you will remember the most from this gracious Eastern Shore manor home.
Beautifully appointed vacation home outside St. Michaels – Property 7022556
- Chesapeake Bay rental - house, 6 bedrooms, sleeps 12, 5 bathrooms, dock boatslip, DVD
- $3,251 - $5,307/week
- Calendar Last Updated On: Nov 8, 2009
Budget friendly cottage getaway, with rowboat included! – Property 7022552
- Chesapeake Bay rental - cottage, 4 bedrooms, sleeps 8, 2 bathrooms, dock boatslip, DVD
- $1,315 - $1,940/week
- Calendar Last Updated On: Nov 8, 2009
A deep water pier with picturesque views make this a truly special spot for a weekend getaway, or mini vacation. Couples love the cozy feeling this cottage gives,...
Enjoy Best Southern Maryland Waterfront Home - with Private Beach and Dock – Property 303386
- Chesapeake Bay rental - house, 4 bedrooms, sleeps 10, 2 bathrooms, river, waterfront, air-conditioning
- $1,500 - $2,350/week
- Calendar Last Updated On: Nov 5, 2009
Welcome to our Cobb Island, Maryland Vacation Rental Home, on the waterfront in Southern Maryland, one hour from Washington D.C.
Sweeping Chesapeake Bay views with Sandy Beach,dock, pool. – Property 7004795
- Chesapeake Bay rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, dock boatslip, DVD
- $1,913 - $3,998/week
- Calendar Last Updated On: Nov 8, 2009
This expansive five bedroom home provides all the modern conveniences of home only with Eastern Chesapeake Bay as the setting.
Fantastic Family Compound 1/2 mile to St. Michaels, Pool, Dock, Hot tub – Property 7004796
- Chesapeake Bay rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, dock boatslip, DVD
- $2,839 - $6,271/week
- Calendar Last Updated On: Nov 8, 2009
Located on the outskirts of the town proper of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway.
