Chestertown Holiday House Rentals from AU$153: Search Holiday Homes

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An aerial view of a town with a river, buildings, and surrounding greenery.

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Our top choices for Chestertown holiday homes

A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

A deck with outdoor furniture, a potted plant, and a house in the background.

A house with a blue door, a front porch, and a garden with various plants and flowers.

A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.

1. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

The price is AU$404

AU$404

includes taxes & fees

5 Oct - 6 Oct

Cozy 1-bedroom in-law suite in lovely Chestertown with AC

A garden with a variety of plants and a small bridge.

A covered patio with a table and chairs, a grill, and a decorative railing.

A two-story house with a porch, a chimney, and a flagpole.

A bedroom with a large bed, wooden bookshelves, a tall black column, and large windows.

2. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town

Chestertown

10.0 out of 10, Exceptional, (75 reviews)

10/10

Exceptional

(75 reviews)

"Perfect location for exploring the cutest town. "

Mandy D.

The price is AU$682

AU$682

includes taxes & fees

22 Sept - 23 Sept

Wren Retweet- Country Estate in Center of C’Town

A building with a gabled roof and a circular vent on the roof.

A room with a Galaxy S22, a table with chairs, a refrigerator, and a window with curtains.

A hotel room with a window, a door with a mirror, a wall-mounted thermostat, and a warning sign about overheating.

A bathroom with a glass-enclosed shower, a sink, and a mirror.

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall

10.0 out of 10, Exceptional, (65 reviews)

10/10

Exceptional

(65 reviews)

"Perfect little place for our weekend stay!"

Diane V.

The price is AU$434

AU$434

includes taxes & fees

17 Sept - 18 Sept

BAYSIDE BUNGALOW

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

A dining area with a wooden table, teal chairs, and a bowl of green apples.

A kitchen with white cabinets, a microwave, a sink, and a window with a view of a house.

A dining area with a wooden table and teal chairs, a ceiling fan, and a window with blinds.

4. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor

Rock Hall

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Great spot, close to everything in town - had a nice visit!"

Adam S.

The price is AU$565

AU$565

includes taxes & fees

1 Oct - 2 Oct

Bayside Cottage steps from Rock Hall Harbor

A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

A kitchen with white cabinets, a wooden island, and a washing machine.

A neatly made bed with a white comforter and pillows, a television on a stand, a patterned curtain, and a wall art piece.

A bedroom with a bed, a bedside table with a lamp, a door, and a wall-mounted light fixture.

5. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC

Aberdeen

7.6 out of 10, Good, (19 reviews)

7.6/10

Good

(19 reviews)

"Nice place"

christine

The price is AU$153

AU$153

includes taxes & fees

29 Sept - 30 Sept

Charming 2-bedroom house in Aberdeen with WiFi and AC

A kitchen with wooden cabinets, a dining table, and a refrigerator.

A two-story brick building with a front porch and a stack of bricks in the foreground.

A cozy dining room with a wooden table and chairs, surrounded by bookshelves and a fireplace.

A two-story brick building with a symmetrical facade, a central entrance, and a well-maintained lawn.

6. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor

Centreville

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "

Emily C.

The price is AU$546

AU$546

includes taxes & fees

23 Sept - 24 Sept

Family Retreat at Lansdowne Manor

A lighthouse with a white exterior, a balcony, and a metal roof.

A bedroom with a wooden floor, a bed with a white and yellow bedspread, a nightstand, and a window with a view of the outdoors.

A spacious living room with a sofa set, a coffee table, and a dining area with a table and chairs.

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

7. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

9.8 out of 10, Exceptional, (47 reviews)

9.8/10

Exceptional

(47 reviews)

"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"

Michelle P.

The price is AU$426

AU$426

includes taxes & fees

21 Sept - 22 Sept

Charming Coastal/Country Home w/3 Acres & Sauna!

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

A kitchen with wooden cabinets, a black refrigerator, a microwave on a wooden shelf, and a sink with a faucet.

A single-story house with a brick foundation and a flat roof.

A bedroom with two single beds, a television on a small table, and a white door.

8. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

9.6 out of 10, Exceptional, (16 reviews)

9.6/10

Exceptional

(16 reviews)

"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "

Robin

The price is AU$712

AU$712

includes taxes & fees

17 Sept - 18 Sept

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

A bed with white and blue pillows, a tufted headboard, and three framed botanical prints on the wall.

A green upholstered bench with a wooden frame, a patterned rug, and a landscape painting on the wall.

A living room with a fireplace, sofa, coffee table, and a TV.

9. Bohemia Manor Farm

Bohemia Manor Farm

3.5 star property

Chesapeake City

The price is AU$535

AU$535

includes taxes & fees

29 Sept - 30 Sept

Bohemia Manor Farm

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with a sink.

An aerial view of a marina with numerous boats docked, surrounded by residential and commercial buildings.

10. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

9.8 out of 10, Exceptional, (55 reviews)

9.8/10

Exceptional

(55 reviews)

"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."

Dawn G.

The price is AU$426

AU$426

includes taxes & fees

21 Sept - 22 Sept

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

A dining area with a wooden table and chairs, a sofa, and a television in the background.

A wooden deck with a white railing, surrounded by a lawn and trees.

A bedroom with a large window, a bed with white bedding, a headboard, and a ceiling light fixture.

11. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage

Bel Air

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Pet friendly."

Claudia L.

The price is AU$467

AU$467

includes taxes & fees

21 Sept - 22 Sept

Watch Deer from a Farm Cottage

A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

A bedroom with a bed, a desk, a chair, a ceiling fan, a TV, and a window.

A spacious living room with a dining area, a sofa set, a TV, and a ceiling fan.

A living room with a brown sofa, a TV mounted on the wall, a lamp on a side table, and a window with blinds.

12. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

Arnold

9.4 out of 10, Exceptional, (40 reviews)

9.4/10

Exceptional

(40 reviews)

"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "

Linda B.

The price is AU$468

AU$468

includes taxes & fees

21 Sept - 22 Sept

Large 2 bedroom house with private parking in a nice neighborhood

A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

A waterfront with a docked boat, a water taxi, and a historic building with a clock tower.

A small patio with a table and two chairs, a brick wall with green foliage, and a wooden ceiling.

A bed with striped bedding, two bedside lamps, and a brick-patterned wall.

13. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio

Fells Point

9.8 out of 10, Exceptional, (100 reviews)

9.8/10

Exceptional

(100 reviews)

"Awesome place, great location"

Mark M.

The price is AU$305

AU$305

includes taxes & fees

27 Sept - 28 Sept

Hidden Fells Point Gem / Private Courtyard Patio

A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

A spacious kitchen with modern appliances, a dining area with a table and chairs, and a view of the outdoors through large windows.

A cabin interior with a kitchen, dining area, and living room.

A two-story building with a front porch and a flagpole with an American flag.

14. The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie

9.2 out of 10, Wonderful, (15 reviews)

9.2/10

Wonderful

(15 reviews)

"Very clean and well stocked Beautiful location Will definitely book againBroken oar and paddle restaurant nearby excellent food and service"

Chris H.

The price is AU$536

AU$536

includes taxes & fees

22 Sept - 23 Sept

The Hideaway Spot- Waterfront w/ Dock on Long Cove

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

A modern living room with a grey sofa, a small coffee table, a TV, and a window with blinds.

A compact bedroom with a bed, a desk, a chair, and a TV.

A pathway leading to a body of water with an American flag, a sign reading 'HERALD HARBOR,' and a 'USE AT YOUR OWN RISK' sign.

15. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access

Herald Harbor

9.8 out of 10, Exceptional, (22 reviews)

9.8/10

Exceptional

(22 reviews)

"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"

Taylor C.

The price is AU$321

AU$321

includes taxes & fees

20 Sept - 21 Sept

Cute, Cozy 2-bedroom house near Annapolis with water access

A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

A lakeside cabin with a deck and outdoor seating, surrounded by autumn-colored trees.

A cozy living room with a dark-colored sofa, a wooden coffee table, and a dining table. There is a large window with a view of the outdoors, and a ceiling fan is visible.

A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

16. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville

9.8 out of 10, Exceptional, (162 reviews)

9.8/10

Exceptional

(162 reviews)

"Family friendly, clean, quiet and great place to relax and watch the birds."

Teresa M.

The price is AU$772

AU$772

includes taxes & fees

17 Sept - 18 Sept

5-bedroom vacation home 5 minutes from historic Charlestown

A row of brick townhouses with a tree in the foreground, a sidewalk, and string lights.

A modern kitchen with stainless steel appliances, white cabinetry, a built-in oven, microwave, and a dishwasher.

A narrow street lined with brick buildings, illuminated by string lights, with a tree and parked cars visible.

A bed with white bedding, a nightstand with a lamp, a large potted plant, and a window with curtains.

17. Patterson Park Gem, Walk Everywhere

Patterson Park Gem, Walk Everywhere

Patterson Place

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"House was clean and host very responsive. Beds were comfortable. It wasn’t as close to Fellspoint as I hoped but easy drive. "

Deborah O.

The price is AU$367

AU$367

includes taxes & fees

22 Sept - 23 Sept

Patterson Park Gem, Walk Everywhere

A hot tub area with a covered patio, stone seating, and a view of the backyard.

A kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a window providing a view of greenery.

A bedroom with a bed, nightstands, a ceiling fan, and two windows with blinds.

A dining room with a wooden table, black chairs, a patterned rug, and a chandelier.

18. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!

Green Haven

10.0 out of 10, Exceptional, (35 reviews)

10/10

Exceptional

(35 reviews)

"10/10 stars! We had a wonderful stay! It was very clean and well organized! Loved it"

Amy L.

The price is AU$672

AU$672

includes taxes & fees

8 Oct - 9 Oct

Idyllic Pasadena Retreat with Garden + Hot Tub!

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

A dining table set with plates, glasses, and a wine bottle, surrounded by chairs and a decorative vase.

A waterfront scene with a sailboat docked at a pier, buildings in the background, and a clear sky.

A beach with a bridge in the background during sunset.

19. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Cape Saint Claire

9.0 out of 10, Wonderful, (16 reviews)

9.0/10

Wonderful

(16 reviews)

"Quiet neighborhood, worked well for our group of 8."

Jennifer H.

The price is AU$949

AU$949

includes taxes & fees

17 Sept - 18 Sept

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

A dining area with a round table and chairs, a small wooden desk with a chair, and a refrigerator in the background.

A bedroom with a bed, a door, and a carpet.

A living room with a sofa, coffee table, and a rug.

20. Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Berea

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

"Host was very friendly and the space was large and clean! "

Mia H.

The price is AU$421

AU$421

includes taxes & fees

30 Sept - 1 Oct

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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