Chesapeake Bay Vacation Home Rentals(25)
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
It is all about the view - Updated, Decks, Shaded Back Yard, Dock
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$495 -
$605
per night
3 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
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
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
Contemporary Cottage on quiet creek, waterside pool, tranquil views
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$675 -
$775
per night
2 - 7 night Minimum Stay
- 3 BR,
- 2 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
Sprawling Multi-Family Home with all the best amenities--pool, hot tub, dock, kayaks and more!
- 6 Bedrooms,
- 6 Half Baths, Sleeps 23
- 6 BR,
- 6 HF BA,
- Sleeps 23
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
$672 -
$972
per night
2 - 7 night Minimum Stay
- 5 BR,
- 3 BA,
- Sleeps 10
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
In the Heart of Chesapeake Bay on Maryland’s Scenic Eastern Shore
- 7 Bedrooms,
- 7 Bathrooms,
- 1 Half Bath, Sleeps 14
$2,000 -
$2,500
per week
3 night Minimum Stay
- 7 BR,
- 7 BA,
- 1 HF BA,
- Sleeps 14
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
Magical Bayfront Home
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$350 -
$425
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
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
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
Fishing Cove Private Waterfront Retreat with Pool and Pier
- 8 Bedrooms,
- 6 Bathrooms, Sleeps 22
- 8 BR,
- 6 BA,
- Sleeps 22
Knapps Narrows Waterfront Getaway W/ Boatslip!
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
$250 -
$350
per night
3 night Minimum Stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Treasure the Chesapeake Bay w/Beachfront Home
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$1,950
per week
7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Welcome Home to Sunset Bay
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 13
$600 -
$700
per night
3 night Minimum Stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 13
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