67 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay House Rentals with pool(67)

67 Results
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
(34)
$745 - $1,250
per night
3 - 7 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
(17)
$450 - $750
per night
2 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night minimum stay
(37)
$750 - $785
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(3)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 15
3 night minimum stay
(7)
$700 - $2,250
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
3 - 7 night minimum stay
(9)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
(24)
$2,395 - $3,940
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(43)
  • 5 BR,
  • 5 BA,
  • Sleeps 12
7 night minimum stay
(13)
$3,593 - $6,180
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
(9)
$2,557 - $4,218
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(34)
$786 - $800
per night
3 - 7 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 12
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 night minimum stay
(18)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night minimum stay
(19)
$400 - $600
per night
2 - 5 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
2 - 5 night minimum stay
(19)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 - 7 night minimum stay
(15)
$475 - $600
per night
3 - 7 night minimum stay
  • 6 BR,
  • 3 BA,
  • Sleeps 12
3 - 7 night minimum stay
(4)
$650 - $700
per night
3 - 7 night minimum stay
  • 7 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
3 - 7 night minimum stay
(7)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 9
7 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
(12)
$430 - $771
per night
2 - 7 night minimum stay
  • 8 BR,
  • 6 BA,
  • Sleeps 22
2 - 7 night minimum stay
(19)
$200 - $250
per night
2 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 4 night minimum stay
$2,400 - $2,900
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
7 night minimum stay
(4)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 6 night minimum stay
(26)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 - 7 night minimum stay
(6)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
2 Reviews
$449 - $741
per night
2 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 20
2 - 7 night minimum stay
(18)
$2,575 - $4,120
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(30)
 

Recent Chesapeake Bay Reviews

Great vacation rental for large groups!

5 of 5
My family and I had an excellent stay here over Thanksgiving. There was plenty of space, comfortable accommodations, and a beautiful kitchen/dining room for our Thanksgiving feast. It is conveniently located near adorable St. Michael's, but we hardly left the house because it was so relaxing. Would stay here again in a heartbeat.
  • Submitted: Jan 18, 2015
  • Stayed: Nov 2014

What a sensational property!

5 of 5
This home had everything we needed to hold our family Thanksgiving reunion, and, I mean everything. From comfortable bedrooms, social living space and wonderful dining and kitchen space to all of the accoutrements needed to prepare a Thanksgiving feast. The owner is meticulous with the intricacies of managing a vacation rental home, from rental engagement through post occupancy. She was accessible and proactive and made sure the home would fit our specific needs. AND the view is sensational from multiple rooms. A truly peaceful and inspiring setting. My family looks forward to retuning in the future.
  • Submitted: Dec 4, 2014
  • Stayed: Nov 2014

Absolutely Perfect

5 of 5
I just returned from a guys' getaway weekend here and was thrilled with the experience. It was such a slice of heaven that nobody wanted to leave! Amos and Liz have really thought of everything in terms of comforts (plenty of towels, yard games in the garage, kayaks, wifi, DirecTV, etc etc). The photos on here don't do it justice (nor do the ones I took myself) because you just can't capture the 360 degrees of awesomeness surrounding you at all times. I'll definitely be back!
  • Submitted: Oct 28, 2014
  • Stayed: Oct 2014