Chester Holiday House Rentals from AU$120: Search Holiday Homes

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A boat docked at a pier during twilight with a city skyline in the background.

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Our top choices for Chester holiday homes

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

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

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

1. 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$400

AU$400

includes taxes & fees

7 Sept - 8 Sept

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

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

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

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

2. 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$402

AU$402

includes taxes & fees

8 Sept - 9 Sept

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

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

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

A spacious living room with a fireplace, a ceiling fan, and a large window.

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

3. 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$572

AU$572

includes taxes & fees

10 Sept - 11 Sept

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

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

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

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

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

4. 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$466

AU$466

includes taxes & fees

7 Sept - 8 Sept

Large 2 bedroom house with private parking in a nice neighborhood

A beach with chairs and a pier in the background.

A hot tub with a white deck and railing, surrounded by trees and a house in the background.

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

A living room with a sofa, coffee table, and a ceiling fan. There is a staircase with a railing leading to an upper level.

5. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

9.6 out of 10, Exceptional, (19 reviews)

9.6/10

Exceptional

(19 reviews)

"The perfect off-season get-away! "

Pamela B.

The price is AU$687

AU$687

includes taxes & fees

9 Sept - 10 Sept

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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

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.

A room with a window, a door labeled "SAUNA", and a bed with a floral bedspread.

6. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall

10.0 out of 10, Exceptional, (64 reviews)

10/10

Exceptional

(64 reviews)

"Perfect little place for our weekend stay!"

Diane V.

The price is AU$431

AU$431

includes taxes & fees

6 Sept - 7 Sept

BAYSIDE BUNGALOW

A deck with outdoor furniture, a red door, and a house with siding.

A modern kitchen with wooden cabinets, stainless steel appliances, a round dining table with stools, and a ceiling fan.

A laundry area with two washers and a dryer, a window with a view of trees, and a shelf with laundry supplies.

A well-maintained lawn, a white picket fence, and a variety of plants including yellow flowers.

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Jut as described. Easy in easy out. Great for a few days with the family."

Joshua T.

The price is AU$529

AU$529

includes taxes & fees

30 Sept - 1 Oct

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

An outdoor patio area with wicker furniture, including two sofas and a coffee table, set on a patterned tile floor with white pebbles.

A kitchen with wooden cabinets, granite countertops, and a central island. There are nautical-themed decorations on the walls.

8. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

8.8 out of 10, Excellent, (3 reviews)

8.8/10

Excellent

(3 reviews)

"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."

William

The price is AU$694

AU$694

includes taxes & fees

7 Sept - 8 Sept

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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

A waterfront property with a dock, sandy beach, and a boat.

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.

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

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

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

Herald Harbor

9.6 out of 10, Exceptional, (20 reviews)

9.6/10

Exceptional

(20 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$331

AU$331

includes taxes & fees

8 Sept - 9 Sept

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

A wooden dock extending into a calm body of water with boats docked at the end.

A two-story house with a porch, a flag, and a welcome sign.

A modern living room with a white sofa, a coffee table, and a dining area with a wooden table and chairs.

A kitchen with wooden flooring, stainless steel appliances, a white door, and a white dining table with chairs.

10. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Historic District

10.0 out of 10, Exceptional, (86 reviews)

10/10

Exceptional

(86 reviews)

"Location, amenities, cleanliness, parking all great!"

Nancy N.

The price is AU$614

AU$614

includes taxes & fees

8 Sept - 9 Sept

Cozy 2br home w/ parking in downtown Annapolis

11. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Historic District

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Very nice, comfortable, convenient property. Host was very communicative. "

Brian L.

The price is AU$888

AU$888

includes taxes & fees

9 Sept - 10 Sept

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

A modern living room with a sectional sofa, a wooden coffee table, a fireplace, and a brick accent wall.

A house with a stone facade, a white door with a glass panel, and a porch with two potted plants.

A modern kitchen with white countertops, wooden cabinets, and stainless steel appliances. There is a dining area with a glass table and chairs, and a view of the outdoors through large windows.

12. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Great house in cute neighborhood. Thanks for a very comfortable stay!"

Paul C.

The price is AU$879

AU$879

includes taxes & fees

13 Sept - 14 Sept

Annapolis Retreat - 7 mins from downtown Annapolis!

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

A spacious living room with a large window, a ceiling fan, and a sofa.

A two-story house with a large front porch and a covered patio area.

A kitchen with white cabinets, a central island with stools, a dining area with a table and chairs, and a view through the glass doors.

13. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

10.0 out of 10, Exceptional, (43 reviews)

10/10

Exceptional

(43 reviews)

"Fantastic, property, location and positive interaction with owner."

David R.

The price is AU$1,893

AU$1,893

includes taxes & fees

7 Sept - 8 Sept

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Three birds perched on a wooden structure by the water.

A wooden deck with picnic tables and umbrellas, a covered seating area with chairs, and a house with large windows.

A cozy living room with a ceiling fan, a dining area with chairs and a table, and large windows offering a view of the outdoors.

14. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

10.0 out of 10, Exceptional, (74 reviews)

10/10

Exceptional

(74 reviews)

"Just what was needed for our weekend stay."

barbara s.

The price is AU$1,807

AU$1,807

includes taxes & fees

7 Sept - 8 Sept

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

A row of colorful townhouses with a brick sidewalk and a street.

A spacious living room with a large grey sofa, a wooden cabinet, and a patterned rug.

A modern kitchen with a microwave, refrigerator, and built-in oven. There is a wooden floor and a hallway leading to another room.

15. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis

Historic District

The price is AU$790

AU$790

includes taxes & fees

7 Sept - 8 Sept

Historic Row Home in Downtown Annapolis

A modern kitchen with a central island, built-in oven, and microwave.

A room with a wooden floor, a desk with a mirror, a lamp, and a door leading to another room.

A covered outdoor dining area with a table set for four, a ceiling fan, and large windows offering a view of a garden and trees.

A modern kitchen with white cabinetry, stainless steel appliances, a central island with seating, pendant lighting, and a view of the outdoors.

16. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Admiral Heights

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"

Tammy L.

The price is AU$732

AU$732

includes taxes & fees

14 Sept - 15 Sept

Cute bungalow blocks to Stadium

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

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

A sandy beach with a calm water body, wooden piers, and a distant shoreline with buildings and trees.

A bedroom with a large bed, a view of the sea, and a wooden window frame.

17. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home

Arundel on the Bay

9.8 out of 10, Exceptional, (76 reviews)

9.8/10

Exceptional

(76 reviews)

"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "

Whitney M.

The price is AU$1,087

AU$1,087

includes taxes & fees

8 Sept - 9 Sept

Charming Annapolis WaterVIEW Home

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

A bedroom with a bed, a television above a fireplace, a wooden chair, and a hanging coat rack.

A red brick building with pink-framed windows and a black door.

A modern kitchen with a brick fireplace, wooden cabinets, and a large TV mounted above it.

18. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!

Historic District

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Fantastic stay! The VRBO was clean, comfortable and had everything I needed. The backyard/patio area was great for relaxing and communication with the host made everything simple. I plan to stay again and whole-heartedly recommend it to others."

Christine A.

The price is AU$1,726

AU$1,726

includes taxes & fees

15 Sept - 16 Sept

Luxe Row Home Steps to USNA Gate 3!

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

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.

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

19. 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$571

AU$571

includes taxes & fees

30 Sept - 1 Oct

Bayside Cottage steps from Rock Hall Harbor

A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

A modern kitchen with wooden cabinets, a stainless steel range hood, and a bar area with bar stools.

A spacious living area with a sofa, ottoman, and dining table. A staircase with a wooden railing leads to another level.

A dining area with a wooden ceiling, a fireplace, and a white mantelpiece.

20. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Annapolis

The price is AU$898

AU$898

includes taxes & fees

9 Sept - 10 Sept

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

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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Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

10/10 Excellent

"Very spacious rooms for the price."

Jake 1-night trip

Posted 1 hour ago

Sonesta ES Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"..........................."

Robert 2-night trip

Posted 2 hours ago

Holiday Inn Express & Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Clean room Helpful staff Great breakfast"

Cynthia 1-night trip

Posted 18 hours ago

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Rooms kept very clean and comfortable. Staff excellent, extremely friendly and helpful. Food very good and good portions."

William 3-night trip

Posted 20 hours ago

DoubleTree by Hilton Hotel Annapolis

The Wildset

10/10 Excellent

"Clean and comfortable. All staff were friendly and helpful. Location made virtually the whole town walkable. Dinner at the restaurant was top notch."

Michael 2-night trip

Posted 3 days ago

The Wildset

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"My third stay. Hotel is clean, staff are friendly and helpful and the location is great."

Emily 1-night trip

Posted 3 days ago

Holiday Inn Express Annapolis East-Kent Island by IHG

Inn at Perry Cabin

10/10 Excellent

"All staff were very pleasant, engaged, and helpful. Everyone seems to genuinely care about making the experience memorable. The property, setting, grounds, and amenities are beautiful and well-maintained."

John 1-night trip

Posted 4 days ago

Inn at Perry Cabin

Best Western Annapolis

10/10 Excellent

"Clean room."

Nery 1-night trip

Posted 7 days ago

Best Western Annapolis

Find out more about Chester

Chester Holiday Homes information

Number of reviews	8,411
Accommodation	614 Holiday Homes
Lowest Price	AU$120
Highest Price	AU$330

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Chester on Expedia.com

Holiday Homes in Chester

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester holiday homes

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

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

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

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

5. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

6. BAYSIDE BUNGALOW

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

8. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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

10. Cozy 2br home w/ parking in downtown Annapolis

11. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

12. Annapolis Retreat - 7 mins from downtown Annapolis!

13. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

14. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

15. Historic Row Home in Downtown Annapolis

16. Cute bungalow blocks to Stadium

17. Charming Annapolis WaterVIEW Home

18. Luxe Row Home Steps to USNA Gate 3!

19. Bayside Cottage steps from Rock Hall Harbor

20. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Find holiday rentals that suit your style

Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

Find out more about Chester

Chester Holiday Homes information

Explore a world of travel with Expedia