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.

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 127 reviews

CHESAPEAKE 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

$170 per night
Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 541 reviews

Sea 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

$83 per night
Guest favorite

Apartment in Greenwood

4.97 out of 5 average rating, 469 reviews

Beach 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

$72 per night

Popular amenities for Tolchester Beach vacation rentals

Other great vacation rentals in Tolchester Beach

Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 107 reviews

Scenic, private 2 room-guest suite, near Bel Air

Feb 2 – 9

$89 per night
Guest favorite

Home in Chestertown

4.92 out of 5 average rating, 36 reviews

Beach House w/ Pool Table, Fire Pit & Office

May 31 – Jun 7

$248 per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 11 reviews

Chesapeake Bay Retreat w/ Views!

Aug 13 – 20

$238 per night
Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

Aug 20 – 27

$125 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 35 reviews

Waterfront house with private dock & kayaks!

Dec 4 – 11

$215 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 16 reviews

Goose Haven, new waterfront house on Fairlee Creek

Jun 21 – 28

$482 per night
Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 99 reviews

Red, White & Waterview Studio Apt with pool

Nov 26 – Dec 3

$119 per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 64 reviews

Waterfront historic district 1BR Apartment

Feb 3 – 10

$141 per night
Guest favorite

Home in Abingdon

4.95 out of 5 average rating, 58 reviews

AbingdonBB

Jan 6 – 13

$78 per night
Guest favorite

Home in Sparrows Point

5.0 out of 5 average rating, 51 reviews

Pristine Waterfront Home with Bay Views for Miles

Aug 7 – 12

$495 per night
Superhost

Home in Chestertown

4.92 out of 5 average rating, 12 reviews

Langford Creek | Waterfront w/ HOT TUB + Fire Pit!

Feb 7 – 14

$497 per night
Guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 43 reviews

Long Beach Cottage, (romantic couple’s getaway)

Nov 26 – Dec 3

$404 per night

Destinations to explore

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  3. Maryland
  4. Kent County
  5. Tolchester Beach