Chesapeake Bay Vacation Home Rentals Pet Friendly(96)
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
Renovated Waterfront Farm House on 25 Acres with Pool
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$730 -
$872
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 -
$921
per night
2 - 7 night minimum stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 13
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
Updated Historic Sprawling Waterfront Estate minutes to Oxford
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 10
$717 -
$993
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
$400 -
$785
per night
3 - 7 night minimum stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
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
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 8
$475 -
$750
per night
2 - 7 night minimum stay
- 4 BR,
- 2 BA,
- Sleeps 8
Magical Bayfront Home
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$286 -
$425
per night
2 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 8
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
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
$200 -
$350
per night
3 night minimum stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Great amenities---close to town, pool, dock, hot tub!
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$640 -
$790
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
Chesa. Bay Vacation Rental, quiet, beachy, open, bay view, LAST MIN. SPECIALS!
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 12
$300 -
$450
per night
2 - 7 night minimum stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 12
Chesapeake Bay retreat on Flag Harbor Marina. Fantastic!
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
- 4 BR,
- 2 BA,
- Sleeps 10
Relaxing Family Retreat with Dock and Pool
- 6 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 14
$400 -
$800
per night
2 night minimum stay
- 6 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 14
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
- 7 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 18
$543 -
$686
per night
3 - 7 night minimum stay
- 7 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 18
Tilghman Island Manor - Tranquility
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Bayberry Cove Private 11 Acre Chesapeake Waterfront 5 Bedroom w/Pool & Hot Tub
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 15
$357 -
$2,500
per night
2 - 7 night minimum stay
- 5 BR,
- 4 BA,
- Sleeps 15
Osprey's Nest, Spacious, Peaceful, Bay Views, Sunrises, Relaxing
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$300 -
$450
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 10
Expansive Georgian Colonial on Green Cove Point
- 7 Bedrooms,
- 4 Bathrooms, Sleeps 18
$927 -
$1,339
per night
2 - 7 night minimum stay
- 7 BR,
- 4 BA,
- Sleeps 18
Waterfront Pool, poolhouse, dock, kayak, paddleboards, billiards, ping pong
- 6 Bedrooms,
- 5 Bathrooms, Sleeps 12
$1,031 -
$1,276
per night
2 - 7 night minimum stay
- 6 BR,
- 5 BA,
- Sleeps 12
Large 5BR home with pool, dock, sandy beach. Great Kayaking location!
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$485 -
$790
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
Easy to Love, Hard to Leave
- 7 Bedrooms,
- 7 Bathrooms,
- 1 Half Bath, Sleeps 22
$1,059 -
$1,361
per night
2 - 7 night minimum stay
- 7 BR,
- 7 BA,
- 1 HF BA,
- Sleeps 22
Enjoy the Water? Fishing, Crabbing, Boating? Here it is!
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
$2,200
per week
7 night minimum stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
HGTV Dream Home--Waterfront Pool, Hot Tub, Sandy Beach!
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 6
$810 -
$942
per night
2 - 7 night minimum stay
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 6
Splendid 1940s Country Garden Estate. Enormous Views, Pool, Boathouse and De
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 8
$562 -
$705
per night
2 - 4 night minimum stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 8
Nanticoke Farmhouse - Luxury and Charm at the Chesapeake Bay
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$175 -
$255
per night
2 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
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