Eastern Shore Vacation Rentals | Chesapeake Rentals | Maryland Vacation Rentals | Chesapeake Bay Vacation Rentals

Have fun browsing our entire portfolio. ESVR has the largest professionally managed portfolio of homes on the middle Eastern Shore. We represent everything from a two bedroom waterfront cottage to classic 5BR Chesapeake Bay Estate home, and even a few larger multi-family homes. This list encompasses all ESVR homes from St Michaels, Tilghman Island, Oxford, Easton, Cambridge and Chestertown, with all price ranges and amenities represented. To narrow your search criteria feel free to give us a call or search by specific property type. Don't Let Another Season Pass You By!

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Anchorage	St. Michaels Easton	8	No	Private Pool	60' Dock 4' MLW	Virtual Tour	Floor Plan	Map It
Barths Cottage	St. Michaels Easton	8	Yes	Private Pool	40' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Bayutiful	St. Michaels Tilghman Island	6	Yes	No	30' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Blue Gates	Oxford/Easton	10	No	Private Pool	40' Dock 4' MLW	Virtual Tour	Floor Plan	Map It
Bushey Heath Farm	St. Michaels Easton	8	Yes	Private Pool	77' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
Cabin Cove Manor	St. Michaels Tilghman Island	8	Yes	Private Pool	20' Dock 2.5' MLW	Virtual Tour	Floor Plan	Map It
Captains Cove	St. Michaels	10	No	Private Pool & Hot Tub	100' Dock 6' MLW	Virtual Tour	Floor Plan	Map It
Captains Quarters	Cambridge	22	No	Private Pool	60' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Caulk's Cove	St. Michaels Bozman/Neavitt	8	Yes	No	180' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
Cedar Point	Cambridge	8	Yes	Private Pool	75' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Chesapeake Pines	St. Michaels Easton	8	No	No	75' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Choptank Cottage	Tilghman Island	6	Yes	No	25' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Clearview	Tilghman Island	7	Yes	Private Pool & Hot Tub	60' Dock 3.5' MLW	Virtual Tour	Floor Plan	Map It
Cods Point	Cambridge/Trappe	12	Yes	No	172' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
Crabbiest Cottage	St. Michaels	6	Yes	Community Pool Nearby	100' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
East Bonfield Farm	Oxford	10	Yes	Private Pool	50' Dock 3' MLW Sandbar	Virtual Tour	Floor Plan	Map It
Easton Hideaway	Easton	6	Yes	Private Pool	140' Dock 3.5' MLW	Virtual Tour	Floor Plan	Map It
Graceful View	St. Michaels Bozman/Neavitt	6	Yes	No	75' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Green Shadow Barn	St. Michaels Easton	8	No	Private Pool	75' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
Hampden	Oxford/Trappe	14	Yes	Private Pool & Hot Tub	125' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
Harbor Hideaway	St. Michaels	4	Yes	Community Pool Nearby	No	Virtual Tour	Floor Plan	Map It
Harbor Hill	Oxford	6	Yes	No	125' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
Hudson Manor	Cambridge	22	Yes	Private Pool	150' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Lee Haven	St. Michaels Easton	10	No	Private Pool	50' Dock 4' MLW	Virtual Tour	Floor Plan	Map It
Macks Landing	St. Michaels Tilghman Island	6	Yes	Private Pool	70' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Mariners Point	Tilghman Island	6	Yes	No	No	Virtual Tour	Floor Plan	Map It
Martini Cottage	Oxford	4	Yes	No	Slip at Marina Can Be Rented	Virtual Tour	Floor Plan	Map It
Miles Aweigh	St. Michaels	6	Yes	Private Pool	120' Dock 6' MLW	Virtual Tour	Floor Plan	Map It
My Blue Heron	St. Michaels Easton	6	No	No	75' Dock 2.5' MLW	Virtual Tour	Floor Plan	Map It
Neavitt Manor	St. Michaels Bozman/Neavitt	6	Yes	Private Pool	50' Dock Shallow Water	Virtual Tour	Floor Plan	Map It
Osprey Point	St. Michaels Easton	8	Yes	Private Pool	80' Dock 4.6' MLW	Virtual Tour	Floor Plan	Map It
Pandion	St. Michaels Bozman/Neavitt	5	No	Hot Tub	No	Virtual Tour	Floor Plan	Map It
Pier Street	Oxford	7	Yes	Hot Tub	75' Dock 5' MLW	Virtual Tour	Floor Plan	Map It
Pines at Barrett Cove	St. Michaels	6	Yes	Private Pool & Hot Tub	50' dock 3.5' MLW	Virtual Tour	Floor Plan	Map It
Pride and Joy Cottage	Oxford	6	Yes	No	No	Virtual Tour	Floor Plan	Map It
Quarter Cove	St. Michaels Easton	8	Yes	Private Pool	165' Dock 4' MLW	Virtual Tour	Floor Plan	Map It
River House on Moon Bay	Chestertown	8	No	No	Mooring Buoy	Virtual Tour	Floor Plan	Map It
River Marsh Condominium	Cambridge	4	Yes	Hyatt Spa and Restaurant Access	Slip at Marina	Virtual Tour		Map It
Simplicity Cottage	Tilghman Island	4	Yes	No	45' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Sunrise Cove	St. Michaels	8	Yes	Private Pool & Hot Tub	120' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Sunset Bay	Cambridge	16	Yes	Private Pool & Hot Tub	75' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Swan Harbor	St. Michaels	8	Yes	Community Pool Nearby	100' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Swift Haven	St. Michaels Bozman/Neavitt	9	Yes	Private Pool Heated	180' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Sycamore Acres	St. Michaels Easton	12	No	Private Pool	100' Dock 2.5' MLW	Virtual Tour	Floor Plan	Map It
The Cove	St. Michaels Easton	8	No	Private Pool	160' Dock 4' MLW	Virtual Tour	Floor Plan	Map It
The Orchard	St. Michaels Easton	8	No	Private Pool & Hot Tub	75' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
The Strand	Oxford	6	Yes	No	No	Virtual Tour	Floor Plan	Map It
Three Sheets to the Wind	Tilghman Island	8	Yes	Hot Tub	No	Virtual Tour	Floor Plan	Map It
Up The Creek	St. Michaels Easton	7	Yes	No	100' Dock 3' MLW	Virtual Tour	Floor Plan	Map It
Whale Tail	St. Michaels Bozman/Neavitt	10	No	Private Pool	75' Dock 2' MLW	Virtual Tour	Floor Plan	Map It
Willows on the Miles	St. Michaels Easton	11	Yes	Private Pool	100' Dock 2.5' MLW	Virtual Tour	Floor Plan	Map It
Windswept	St. Michaels	8	Yes	Private Pool	No	Virtual Tour	Floor Plan	Map It
Winter Bottom Point	St. Michaels Bozman/Neavitt	7	No	No	50' Dock 2' MLW	Virtual Tour	Floor Plan	Map It

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