Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay Pet Friendly Cottage Rentals(54)

54 Results
$434 - $515
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 - 3 night minimum stay
(63)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(27)
$234 - $390
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(78)
$439 - $632
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(34)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 night minimum stay
(27)
$250 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(33)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
7 night minimum stay
(5)
$505 - $663
per night
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
2 - 3 night minimum stay
(43)
$506 - $594
per night
2 - 3 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(30)
$467 - $545
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(51)
$389 - $636
per night
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
(17)
$100 - $175
per night
1 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
2 night minimum stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night minimum stay
(12)
$99 - $175
per night
1 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
1 - 4 night minimum stay
(18)
$373 - $586
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(31)
$551 - $644
per night
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 - 3 night minimum stay
(19)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 - 3 night minimum stay
(18)
$137 - $260
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(24)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(10)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
1 Review
$541 - $723
per night
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 3 night minimum stay
(4)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(3)
$506 - $594
per night
2 - 3 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 3 night minimum stay
(3)
  • 7 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 3 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 5
2 - 3 night minimum stay
2 Reviews
$115 - $125
per night
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night minimum stay
(7)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
$300
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(7)
 

Recent Chesapeake Bay Reviews

Very nice . . .

5 of 5
Our stay at the cottage was not long enough. The tasteful decorations, supplies on hand combined with the beautiful weather made our first trip to this area a memorable one. Our dog had a fantastic time playing in the water, running the beach and trying to catch sea creatures. The deck off the side was just right for coffee, cocktails and talking. The overall peace and tranquility of the area was amazing. We are looking forward to returning next year. Thank you for helping us celebrate our trip.
  • Submitted: Oct 3, 2014
  • Stayed: Sep 2014

Loverly!

5 of 5
A wonderful week in a wonderful cottage in a wonderful town. Steps to a small harbor and another block to the river view. Walked into town for great shops and restaurants (Don't miss Gregorio Gallery for great photos and gifts and Gina's at the top of the street for great shrimp tacos and crab dip!) Nice bike rides on the nature trail a few blocks from the cottage. Open the windows at night for the sound of silence interrupted only by the sounds of nature. The setting was ideal! Thanks!
  • Submitted: Sep 1, 2014
  • Stayed: Aug 2014

Awesome time

5 of 5
I spent 10 days in Deal Island's cottage and wished I could have stayed another 10. The cottage was clean and quaint and had everything I needed, I particularly enjoyed the screen porch where a breeze from the bay could be felt almost anytime. I was worried at first that the cottage would be too hot to sleep at night but the window ac was more than enough And I had to shut it off as it became too cold. Mo the owner and all the locals I met were welcoming and friendly and the island was quiet without all the beach traffic and tourist traps, just what I was looking for. My dogs had a great time walking and sleeping on the little beach where we spent much of our time since the weather was great, I read, ate and relaxed. Hopefully I can go back next year
  • Submitted: Aug 16, 2014
  • Stayed: Aug 2014