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 6 – 13
Apartment in Pasadena
4.99 out of 5 average rating, 541 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
Apartment in Greenwood
4.97 out of 5 average rating, 469 reviewsBeach Highway Hobby Farm
We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)
Sep 14 – 21
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
Guest suite in Forest Hill
5.0 out of 5 average rating, 107 reviewsScenic, private 2 room-guest suite, near Bel Air
Feb 2 – 9
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!
Aug 13 – 20
Apartment in Rock Hall
4.96 out of 5 average rating, 47 reviewsBayside bungalow cottage by the sea
Aug 20 – 27
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
Jun 21 – 28
Casa particular in Chestertown
4.93 out of 5 average rating, 99 reviewsRed, White & Waterview Studio Apt with pool
Nov 26 – Dec 3
Apartment in Chestertown
5.0 out of 5 average rating, 64 reviewsWaterfront historic district 1BR Apartment
Feb 3 – 10
Home in Abingdon
4.95 out of 5 average rating, 58 reviewsAbingdonBB
Jan 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
Home in Chestertown
4.92 out of 5 average rating, 12 reviewsLangford Creek | Waterfront w/ HOT TUB + Fire Pit!
Feb 7 – 14
Cottage in Charlestown
4.98 out of 5 average rating, 43 reviewsLong Beach Cottage, (romantic couple’s getaway)
Nov 26 – Dec 3
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