Chesapeake Bay with Pools(119)
Spectacular Corner Unit - Direct Waterfront Condo in Crisfield, Md
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$100 -
$200
per night
3 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$650 -
$700
per night
2 - 3 night Minimum Stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$1,118 -
$1,185
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Pool, hot tub, big water views--what more could you ask for in a cottage
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$583 -
$712
per night
2 - 7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 7
Easy to Love, Hard to Leave
- 7 Bedrooms,
- 7 Bathrooms,
- 1 Half Bath, Sleeps 22
$1,038 -
$1,318
per night
2 - 7 night Minimum Stay
- 7 BR,
- 7 BA,
- 1 HF BA,
- Sleeps 22
Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$650 -
$800
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Renovated Waterfront Farm House on 25 Acres with Pool
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$742 -
$868
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$535 -
$752
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 8
Three level family home restored 1920s Colonial on 25 acres, dock, pool
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 13
$742 -
$912
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 13
Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$727 -
$865
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 8
Updated Historic Sprawling Waterfront Estate minutes to Oxford
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 10
$702 -
$978
per night
2 - 7 night Minimum Stay
- 5 BR,
- 3 BA,
- Sleeps 10
The Point of It All-Near Annapolis, Washington D.C., Baltimore
- 6 Bedrooms,
- 6 Bathrooms, Sleeps 14
$5,425 -
$6,475
per week
7 night Minimum Stay
- 6 BR,
- 6 BA,
- Sleeps 14
Wow! Secluded waterfront home on Maryland's Charming Eastern Shore
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 8
$750
per night
3 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
Special $1,000 Off May and June Weeks
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$800
per night
2 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
2 Weeks Still Open in June - $2000 Off $6300/Week!
- 6 Bedrooms,
- 6 Bathrooms,
- 2 Half Baths, Sleeps 12
$4,900
per week
2 night Minimum Stay
- 6 BR,
- 6 BA,
- 2 HF BA,
- Sleeps 12
Year Round Waterfront Home w/Dock & Pool Sleeps 18
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 18
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 18
Charming Island Home on Chesapeake Bay with Great Water Views
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$185
per night
3 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Year Round Waterfront Estate / Family Reunions - Sleeps 26
- 7 Bedrooms,
- 6 Bathrooms,
- 1 Half Bath, Sleeps 26
- 7 BR,
- 6 BA,
- 1 HF BA,
- Sleeps 26
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 8
$492 -
$750
per night
2 - 7 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 8
Acreage, Amenities and All You Need for Family and Friend Gatherings
- 5 Bedrooms,
- 5 Bathrooms, Sleeps 12
$645 -
$1,135
per night
2 - 7 night Minimum Stay
- 5 BR,
- 5 BA,
- Sleeps 12
1900 Circa Duel Cottages Decorated to Die For
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 6
$592 -
$768
per night
2 - 7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 6
Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 6
$340 -
$600
per night
2 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 6
6.5 Acre Waterfront Retreat!
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 9
$3,850
per week
7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 9
Premium Waterfront Estate Property - $7,500/Week -
- 5 Bedrooms,
- 7 Bathrooms, Sleeps 10
- 5 BR,
- 7 BA,
- Sleeps 10
Endless Waterfront Sunsets on Eastern Bay!!
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 8
$300 -
$550
per night
2 - 3 night Minimum Stay
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
Luxury home with pool and deep water dock.
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
- 4 BR,
- 4 BA,
- Sleeps 8
Fishing Cove Private Waterfront Retreat with Pool and Pier
- 8 Bedrooms,
- 6 Bathrooms, Sleeps 22
- 8 BR,
- 6 BA,
- Sleeps 22
Waterfront Tilghman Island Cottage
- 2 Bedrooms,
- 1 Bathroom, Sleeps 6
$75 -
$175
per night
2 night Minimum Stay
- 2 BR,
- 1 BA,
- Sleeps 6
Waterfront Home in Historic St. Michaels
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
New listing with rural country charm, pool, and a deep water dock
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 10
$350 -
$550
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 10
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