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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
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
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

Other great vacation rentals in Anchorage

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