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Vacation rentals in Anchorage

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Top-rated vacation rentals in Anchorage

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage in Saint Michaels
St. Michaels-Historic Dist. Margaret Wells House
The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.
$209 per night
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Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.
$349 per night
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Rental unit in Chester
Cozy Waterfront Apartment on Kent Island
*We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy this clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to sit & enjoy beautiful water views!
$89 per night
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Other great vacation rentals in Anchorage

Home in Kent Narrows
Chester Riverfront At Kent Narrows
$239 per night
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Guesthouse in Easton
Chill in The Crib! Easton, Maryland
$139 per night
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Cottage in Neavitt
The Middle Point Cottage at Saint Michaels
$150 per night
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Private room in Easton
Quiet and welcoming
$85 per night
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Guest suite in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
$200 per night
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Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
$68 per night
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Home in Saint Michaels
Historic Berkeley Hall in the heart of town
$202 per night
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Home in Saint Michaels
Dr. Miller house. Best location-in the heart town
$179 per night
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Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
$159 per night
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Bungalow in Queen Anne
Adorable 2-bedroom bungalow near Easton, Tuckahoe
$140 per night
Guest suite in Cambridge
"Happy Campers" Waterfront Apartment!
$150 per night
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Private room in Annapolis
Chesapeake Mornings
$50 per night
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