House vacation rentals in Chestertown

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Top-rated house rentals in Chestertown

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Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 129 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.

May 5 – 12

R3,723 ZAR per night

Guest favorite

Home in Lutherville-Timonium

4.93 out of 5 average rating, 132 reviews

* Lovely Gem w/ Perfect Combo of Flair & Class *

This is our 5th Airbnb in the Towson / Lutherville area. We know how important it is to feel comfortable & relaxed when you arrive back from a long day of work, sightseeing, visiting with family members, playing sports, etc. This inspiration is seen throughout this entire house and you'll find the house to be a place to recharge, relax and enjoy high end amenities to include HDTVs in living and bed rooms, fully stocked kitchen, plush bedding, luxury shower fixtures, and more. You have to see it!

Jul 23 – 30

R2,977 ZAR per night

Guest favorite

Home in Annapolis

5.0 out of 5 average rating, 105 reviews

Luxury Waterfront Annapolis/ Private Beach & Dock

Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill & fire bowl. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.

Sep 5 – 12

R19,587 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 155 reviews

Nicely refurbished historic house near town center

Renovated 19th century home with all modern conveniences. First floor bedroom with private bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from both Washington College and the C'town waterfront. 2 primary bedroom suites (one on the second floor has a king bed) 2 more bedrooms with queen beds. 1 loft which is connected to the a 2nd story bedroom has 2 twins. Fenced yard and over an acre of totally private gardens. Fire pit.

Jan 18 – 25

R6,623 ZAR per night

Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 226 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Nov 17 – 24

R8,128 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 104 reviews

Waterfront w/Pier &Walking Distance to Chestertown

This 4 bedroom, 3 bath waterfront home is a terrific place to enjoy time with family and friends. This home has amazing amenities; from the stylish updated renovations and furnishings (some antiques), the screened porch, patio, fire pit, hot tub (Oct - April), sporting equipment, to the spacious, comfortable, indoor & outdoor gathering spaces. The kitchen is well-appointed with gourmet appliances, and plenty of hosting and culinary supplies to savor wonderful meals together at the house.

Feb 6 – 13

R10,413 ZAR per night

Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 199 reviews

Cape St Claire waterfront getaway

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Aug 1 – 8

R2,722 ZAR per night

Guest favorite

Home in Baltimore

4.91 out of 5 average rating, 137 reviews

South Baltimore's Best!

Enjoy a classic Baltimore experience at this centrally-located single bedroom house. Close to Federal Hill, Downtown Baltimore and walkable to both the Orioles and Ravens Stadium. You can walk one mile to the MARC to take the train to DC or stay local and enjoy downtown Baltimore. Ideally situated for an individual or couple, a third person could sleep on the couch, and we have a pack and play and single mattress available for children.

Jun 8 – 15

R1,258 ZAR per night

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 102 reviews

Classic Victorian in Chestertown

A delightful hideaway all to yourself! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Plenty of on-street parking. Professional cleaning before every visit (alcohol and/or bleach solution), combined with complete ventilation of the house 24 hours ahead of arrival.

Dec 10 – 17

R3,669 ZAR per night

Guest favorite

Home in Annapolis

4.96 out of 5 average rating, 110 reviews

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit.

Mar 11 – 18

R2,301 ZAR per night

Guest favorite

Home in Chestertown

4.92 out of 5 average rating, 166 reviews

Historic Chestertown

Lovely home with great indoor-outdoor entertaining space. Fully renovated 3 bed, 2.5 bath. Top of the line open floor plan kitchen/family room. Located in Historic district on the main street only few blocks from restaurants, shops and river front. From May 15, 2022 through Oct 31, 2022 all weekend are a 3 day minimun

Dec 27 – Jan 3

R6,363 ZAR per night

Guest favorite

Home in Chestertown

4.99 out of 5 average rating, 151 reviews

Duchess of Kent: Walk to downtown & College

Location location location! We absolutely love the proximity of our house to campus, the historic district, and the river. Chestertown is charming and there are fun little shops and restaurants around every corner. Our home is cozy and perfect for entertaining. We hope you enjoy it as much as we do!

Nov 9 – 16

R7,411 ZAR per night