Vacation rentals in Tolchester Beach
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Top-rated vacation rentals in Tolchester Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.
Home in Chestertown
4.94 out of 5 average rating, 127 reviewsCHESAPEAKE SUNSETS
Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.
Aug 7 – 14
Apartment in Pasadena
4.99 out of 5 average rating, 542 reviewsSea Dreamer aka Phenomenal Hospitality
Stunning sunrises free in a tranquil, riverfront, apartment with front entrance. Split foyer home, I am upstairs, you are downstairs. 2 separate bedrooms, one overlooking the river. Living room includes dining area, office space, comfy seating, and a massage chair!. Full bath, best showerhead, soaps, shampoos, and towels. Pull out sofa bed for larger parties. Kitchenette has everything necessary to cook with. BWI 20 min, 40 Annapolis, 60 to DC. Patio, fire pit, grill, deck and beach walks.
Nov 16 – 23
Guest suite in Forest Hill
5.0 out of 5 average rating, 107 reviewsScenic, private 2 room-guest suite, near Bel Air
Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.
Mar 7 – 14
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Tolchester Beach vacation rentals
Other great vacation rentals in Tolchester Beach
Home in Chestertown
4.92 out of 5 average rating, 36 reviewsBeach House w/ Pool Table, Fire Pit & Office
May 31 – Jun 7
Home in Rock Hall
5.0 out of 5 average rating, 11 reviewsChesapeake Bay Retreat w/ Views!
Dec 12 – 19
Apartment in Rock Hall
4.96 out of 5 average rating, 47 reviewsBayside bungalow cottage by the sea
Aug 21 – 28
Home in Chestertown
5.0 out of 5 average rating, 35 reviewsWaterfront house with private dock & kayaks!
Dec 4 – 11
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsGoose Haven, new waterfront house on Fairlee Creek
Aug 16 – 23
Casa particular in Chestertown
4.93 out of 5 average rating, 99 reviewsRed, White & Waterview Studio Apt with pool
Nov 27 – Dec 4
Home in Abingdon
4.95 out of 5 average rating, 58 reviewsAbingdonBB
Oct 30 – Nov 6
Apartment in Chestertown
5.0 out of 5 average rating, 64 reviewsWaterfront historic district 1BR Apartment
Jun 6 – 13
Home in Sparrows Point
5.0 out of 5 average rating, 51 reviewsPristine Waterfront Home with Bay Views for Miles
Aug 7 – 12
Cottage in Charlestown
4.98 out of 5 average rating, 43 reviewsLong Beach Cottage, (romantic couple’s getaway)
Nov 28 – Dec 5
Home in Chestertown
4.92 out of 5 average rating, 12 reviewsLangford Creek | Waterfront w/ HOT TUB + Fire Pit!
Feb 7 – 14
Home in Chestertown
5.0 out of 5 average rating, 75 reviewsRiver front cottage with private dock & water fun
Apr 5 – 12
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