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

Holiday Homes in Chester

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chester holiday homes

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

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)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is €246
includes taxes & fees
28 Sept - 29 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.

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)
"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."
United States
Dawn G.
The price is €241
includes taxes & fees
28 Sept - 29 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.

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)
"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. "
United States
Robin
The price is €449
includes taxes & fees
28 Sept - 29 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A building with a gabled roof and a circular vent on the roof.

4. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is €282
includes taxes & fees
28 Sept - 29 Sept
BAYSIDE BUNGALOW
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

5. 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, (41 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. "
United States
Linda B.
The price is €297
includes taxes & fees
30 Sept - 1 Oct
Large 2 bedroom house with private parking in a nice neighborhood
A beach with chairs and a pier in the background.

6. 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)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is €439
includes taxes & fees
28 Sept - 29 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A wooden dock extending into a calm body of water with boats docked at the end.

7. 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)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is €391
includes taxes & fees
5 Oct - 6 Oct
Cozy 2br home w/ parking in downtown Annapolis
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

8. 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)
"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!"
United States
Taylor C.
The price is €193
includes taxes & fees
6 Oct - 7 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

9. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is €347
includes taxes & fees
28 Sept - 29 Sept
Bayside Cottage steps from Rock Hall Harbor
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

10. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is €511
includes taxes & fees
28 Oct - 29 Oct
Annapolis Retreat - 7 mins from downtown Annapolis!
Three birds perched on a wooden structure by the water.

11. 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)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is €1,262
includes taxes & fees
28 Sept - 29 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.

12. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
8.0 out of 10, Very good, (1 review)
"This property was an up and down property for us. The ups: check in process was flawless; cleanliness was as good as an old house can be; and the location was superb. The downs: they say it can sleep ten. Well ten people might sleep but they can’t do much else. There are two baths and the kitchen was fine and although adequate to work with. But there are only four wine glasses and barely five people can sit at the dining room table. So if ten people sleep - they wake up and there are enough...
United States
DEAN F.
Historic Row Home in Downtown Annapolis
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

13. 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)
"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."
United States
Christine A.
Luxe Row Home Steps to USNA Gate 3!
A dining area with a wooden table, chairs, a chandelier, and a clock on the wall.

14. Annapolis Charmer - Perfect Location

Annapolis Charmer - Perfect Location
Historic District
Annapolis Charmer - Perfect Location
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

15. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 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! "
United States
Whitney M.
The price is €610
includes taxes & fees
28 Sept - 29 Sept
Charming Annapolis WaterVIEW Home
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

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

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A modern kitchen with a central island, built-in oven, and microwave.

17. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (12 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
Cute bungalow blocks to Stadium

18. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
Historic Row Home | Hot Tub - 1 Block from Gate 1!

19. 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, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is €527
includes taxes & fees
28 Sept - 29 Sept
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

20. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Loved everything about it but especially the staff was so friendly and accommodating!"
petra 6-night trip
Posted 13 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Chester

Chester Holiday Homes information

Number of reviews
475
Accommodation
616 Holiday Homes
Lowest Price
€193
Highest Price
€1,262