Chesapeake Bay

Showing

Renovated Luxury Waterview House - North Beach vacation rentals
1 / 9

$250

Book

Renovated Luxury Waterview House

North Beach house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to beach, boardwalk, …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

$1,100

Inquire

Yr Round Estate on Bay / Family Reunions Sleeps 28

Cambridge villa
7 BR / 6 BA / Sleeps 28 | Quick view
Excellent5 Reviews

Details

Reviews

(5)

Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates up to 28 people and …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

Great hospitality...

Left on Apr 24, 2012 for a stay in April 2012

The house is well decorated and spacious, fantastic for family gatherings. We had a great experience that will be remembered for the rest of our lives.

This property had all you needed for a great family vacation, but above all, the owner is a master of hospitality - he was very accommodating to every request we had.

I hope to go back to this house for another week soon.

$449

Inquire

Waterfront Chespeake Bay Retreat

Cambridge house
7 BR / 5 BA / Sleeps 18 | Quick view
Excellent11 Reviews

Details

Reviews

(11)

New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal for large family …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(11)

Wondeful home - Great for Fishing!

Left on May 04, 2009 for a stay in April 2009

We had an amazing week at this gorgeous house. The house is brand new and immaculate. Everything in it is brand new!! It truly felt like home. The owners are amazing - it was a warmer week than expected and they went out of their way to open the pool for us. They also gave a lot of great recommendations on places to eat. We took out the boat and the kids had a great time fishing and …

$449

Inquire

Stunning, Newer Chesapeake Waterfront Rental

Cambridge house
6 BR / 5 BA / Sleeps 16 | Quick view
Excellent9 Reviews

Details

Reviews

(9)

Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge, Easton, Oxford & St. …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(9)

GREAT Vacation!

Left on May 05, 2009 for a stay in August 2008

We really had a GREAT stay. The house is much more than we expected; it's very well done and comfortable (the owner was nice as well). The water views are amazing and the grounds perfect. We swam, fished, crabbed, biked and boated - had a great time off property as well. This was a TOP notch vacation.- thanks!

Chesapeake Bay Sunrises AND Sunsets - Westover vacation rentals
1 / 22

$150

Book

Chesapeake Bay Sunrises AND Sunsets

Westover house
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Located in Frenchtown, MD, 30 min south of Salisbury, MD on Chesapeake Bay's Eastern Shore. This is a private home on an island in the middle of ten thousand acres of salt marsh and near a national wildlife management area. Views from the bedroom, enjoy waterfront sunrises, water views from the living room & dining …
  • Waterfront
  • Ocean or water views
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly

$350

Inquire

Large Historic Home On Harbor in St. Michaels

Saint Michaels house
7 BR / 4 BA / Sleeps 11 | Quick view
Excellent6 Reviews

Details

Reviews

(6)

The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and shops in St. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(6)

This was the perfect home for a week of wedding planning and family relaxation time.

Left on Jul 23, 2014 for a stay in June 2014

Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time together finalizing wedding plans. The stay at the Harrison Home added so many memories to the already fond memories of a wedding. We cooked together with all the amenities in the kitchen. The home was so large we could …

$225

Book

Cobb Island Waterfront Home with Beach & Dock

Cobb Island house
4 BR / 2 BA / Sleeps 9 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Welcome to our Cobb Island, Maryland Home, on the waterfront in Southern Maryland, one hour from Washington D.C. - the perfect spot to spend your next relaxed family vacation enjoying water oriented activities and fabulous river views. We have been renting this house to more than 200 families since 1999 and have many…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Great Waterfront Rental for families and groups of friends

Left on Dec 28, 2011 for a stay in July 2010

I only have great things to say about Ed Mullan's Cobb Island rental.
Having stayed there for several weekends, I can attest to the
comfortable and well-appointed house, fantastic location close to
Washington, DC, and abundance of fun activities at the house and
surrounding area. The property is ideal for families as well as groups of friends. Both the indoor and outdoor areas are conducive for …

$450

Book

Beautiful St. Michaels House Steps from Water and Town

Saint Michaels house
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent6 Reviews

Details

Reviews

(6)

Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath, second floor has one …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(6)

Great Location, Great House, Great Time

Left on Jul 13, 2014 for a stay in July 2014

This house was perfect for a large family and very convenient for walking to sites in town. The house had a well equipped kitchen, nice backyard and barbecue grill. Within walking distance to local parks and public pool. We had nice holiday!

1 / 4

$575

Book

Red Point Lighthouse

North East house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Custom lighthouse with 4 bedrooms and 4 baths overlooking the Chesapeake Bay. Within one hour from Baltimore, MD, Wilmington DE, and Lancaster, PA. Perfect for large families, weddings, ect.
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Fireplace
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

$250

Book

Unique, Affordable Nature-Oriented Getaway Home

Cambridge house
3 BR / 2 BA / Sleeps 6 | Quick view
Average1 Reviews

Details

Reviews

(1)

Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide covered front porch and …
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Nice house but it is not on the water

Left on Oct 26, 2012 for a stay in July 2012

This is a lovely older house with lots of room for families. We are very grateful that she accepts dogs and even better that the house is so clean you can't tell that dogs have stayed there. The electronics are a bit old but useable and there is no wifi. There are bikes available for use and the area would be great for bike riding but in July when we were there it was over 100 every day and …

1 / 10

$250

Book

Relaxation At Its Best!!!!

North East house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Come vacation in this brand-new home in beautiful Elk Neck and you will be glad you did! It is definitely a most gorgeous location and very peaceful, set back in the woods along the river. Elk Neck is approximately eight miles south of the town of North East, MD where there are many neat little shoppes and fabulous …
  • Waterfront
  • Ocean or water views
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask
1 / 20

$240

Book

2 Bedroom Unique Private Waterfront Escape

Easton condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to offer! The …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer

    $180

    Inquire

    Location Location! St Michaels-- In Town Cottage!

    Saint Michaels house
    2 BR / 2 BA / Sleeps 5 | Quick view
    Excellent12 Reviews

    Details

    Reviews

    (12)

    The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (12)

    Crabtastic Great Escape

    Left on Aug 26, 2011 for a stay in August 2011

    This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable.

    I have visited this cottage several…

    1 / 17

    $250

    Book

    Chez Cinquai

    Tilghman house
    4 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet kitchen, custom wood …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    1 / 38

    $759

    Book

    BayCottage Waterfront Vacation Retreat St.Michaels

    Saint Michaels villa
    6 BR / 6 BA / Sleeps 12 | Quick view

    Details

    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are 6 bedrooms, 5.5 …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask
    1 / 18

    $450

    Book

    Historic Waterfront Property with Wi-Fi and Dock

    Saint Michaels house
    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed with 2 twins beds and a…
    • Waterfront
    • Wireless Internet
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    1 / 10

    $190

    Book

    Historic Chestertown, pet-friendly

    Chestertown cottage
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Our Victorian cottage, built in the 1880s and upgraded to more modern standards, offers the best of both worlds: A bit of a rural feel, with a fenced-in side yard and back yard, a lovely porch swing, and ... easy strolling distance to the downtown historic Chestertown. Did you know that the fabulous Garden and Gun …
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Looking for more rentals?


    We're showing only results that match your dates and preferences.


    See all 38 Chesapeake Bay rentals, all 0 Maryland rentals, or start a new search.


    There are no more results in Chesapeake Bay. Top of page