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 7 – 14

R3,722 ZAR per night
Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 542 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

R1,788 ZAR per night
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

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

R1,939 ZAR per night

Popular amenities for Tolchester Beach vacation rentals

Other great vacation rentals in Tolchester Beach

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

R5,403 ZAR per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 11 reviews

Chesapeake Bay Retreat w/ Views!

Dec 12 – 19

R5,050 ZAR per night
Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

Aug 21 – 28

R2,738 ZAR 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

R4,712 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 16 reviews

Goose Haven, new waterfront house on Fairlee Creek

Aug 16 – 23

R10,480 ZAR 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 27 – Dec 4

R2,588 ZAR per night
Guest favorite

Home in Abingdon

4.95 out of 5 average rating, 58 reviews

AbingdonBB

Oct 30 – Nov 6

R1,675 ZAR per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 64 reviews

Waterfront historic district 1BR Apartment

Jun 6 – 13

R3,124 ZAR 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

R10,778 ZAR per night
Guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 43 reviews

Long Beach Cottage, (romantic couple’s getaway)

Nov 28 – Dec 5

R8,307 ZAR 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

R10,869 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr 5 – 12

R9,799 ZAR per night

Destinations to explore

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  3. Maryland
  4. Kent County
  5. Tolchester Beach