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Chesapeake Bay Vacation Home Rentals(169)

169 Results
3 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 13
1 Review
3 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
1 Review
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
(12)
2 - 7 night minimum stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
(8)
  • 7 BR,
  • 6 BA,
  • Sleeps 20
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 17
(12)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(7)
3 night minimum stay
  • 7 BR,
  • 5 BA,
  • Sleeps 12
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
  • 6 BR,
  • 3 BA,
  • Sleeps 12
(3)
  • 6 BR,
  • Sleeps 13
(7)
67 more choices from the HomeAway Network
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
(18)
$350 - $500
per night
2 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
(11)
$200 - $250
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(9)
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
(8)
1 - 2 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
(8)
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
(9)
2 - 3 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
(6)
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(14)
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(5)
$550 - $700
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
(4)
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(4)
2 - 3 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
(24)
2 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
(4)
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
(50)
$250
per night
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 Reviews
2 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 11
(23)
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
(16)
2 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 14
2 Reviews
 

Recent Chesapeake Bay Reviews

WELCOME IS WARM AND KID FRIENDLY!

5 of 5
We are ready to move in! :) Oh how nice it was to stay at this home, we enjoyed every part of it. I particularly liked all the natural elements, wood, fiber, leather - the wood floors with so much character, furniture inside and outside, the decks and eating area in the kitchen where we created so many memories. The woven wall hangings, pillows and upholstry/blankets. The many books, photos, wall art. Being able to open the French doors and breathe in the fresh air that breezed through the house. The children were enchanted and at home with everything this home away from home had to offer. Too many amenities to mention though the library/loft ladder, wagon and swings combined with the beautiful outdoors were magical experiences. Not to mention the enjoyment of everything North Beach has to offer, the farmers market, beach, boardwalk, crabs, Herrington Harbor. I know the next book I will pick up to read, and we didnt even get into the basement or the walkout from there, or walk much around town. I do hope to visit again soon!
  • Submitted: Jul 20, 2014
  • Stayed: Jun 2014

LOVELY AND COMFORTABLE

4 of 5
My husband and I and our two adult children and their friends stayed here for a quiet and relaxing weekend. It was a wonderful escape frm the city....clear skies and sweet air. A beautiful sunrise and plenty of water to view it from with the availability of a canoe.
  • Submitted: Sep 5, 2013
  • Stayed: Aug 2013

ELEGANT, COMFORTABLE, MODERN, RELAXING, EXCELLENT.

5 of 5
Thornton Vineyard was without a doubt one of the most spectacular rental properties I've had the pleasure to enjoy. The house itself is a model of upkeep and renovation to historical structures. It maintained the genteel aura which the circa 1815 property conveys while catering to all of the conveniences of modern, high-class living. The kitchen is all brand new, offering a pleasant work space big enough for the whole family to congregate and enjoy. Almost every room is wired into the whole house stereo; which was one of my favorite features. Furniture, linens, and appointments are all of the highest quality. The master suite alone is larger than many metropolitan apartments! Everything was spotlessly clean. The pool and adjoining pool house was an excellent way to pass the hot summer days while relaxing on this large and private property. Proximity is conveniently close (6 minutes) to Chestertown, while maintaining absolute privacy. The reception provided by leasing agent and property owner upon our arrival was top notch. We were presented with a guided tour of the house and property along with a small selection of fresh local herbs and vegetables. Delightful. Stay here. You'll love it.
  • Submitted: Jul 12, 2013
  • Stayed: Jul 2013