Chester Vacation Homes

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.

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

Stevensville

Michelle P.

HK$2,357 total

includes taxes & fees

14 Oct - 15 Oct

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!

Stevensville

Dawn G.

HK$2,266 total

includes taxes & fees

14 Oct - 15 Oct

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

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

Arnold

Linda B.

HK$2,684 total

includes taxes & fees

12 Oct - 13 Oct

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Pamela B.

HK$3,766 total

includes taxes & fees

20 Oct - 21 Oct

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

5. BAYSIDE BUNGALOW

Rock Hall

Diane V.

HK$2,477 total

includes taxes & fees

12 Oct - 13 Oct

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

HK$10,879 total

includes taxes & fees

11 Oct - 12 Oct

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

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

Herald Harbor

Taylor C.

HK$1,610 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Cape Saint Claire

Jennifer H.

HK$4,916 total

includes taxes & fees

12 Oct - 13 Oct

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

9. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

HK$4,661 total

includes taxes & fees

3 Nov - 4 Nov

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

10. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

HK$10,879 total

includes taxes & fees

11 Oct - 12 Oct

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

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

Annapolis

HK$5,856 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Historic District

Nancy N.

HK$3,731 total

includes taxes & fees

20 Oct - 21 Oct

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

13. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

HK$4,132 total

includes taxes & fees

20 Oct - 21 Oct

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

14. Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

Diane D.

HK$4,706 total

includes taxes & fees

20 Oct - 21 Oct

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

15. Historic Row Home in Downtown Annapolis

Historic District

gina w.

HK$4,402 total

includes taxes & fees

20 Oct - 21 Oct

A two-story house with a red roof, a brick chimney, and a small porch.

16. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...

Suzanne R.

HK$8,269 total

includes taxes & fees

11 Oct - 12 Oct

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

Historic District

Tracie B.

HK$4,500 total

includes taxes & fees

20 Oct - 21 Oct

A spacious living room with a high ceiling, large windows, and a ceiling fan.

18. The Harness Creek Retreat in Annapolis

Hillsmere

HK$3,328 total

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

19. Mins to DTA - King Beds - Parking

Annapolis

Nader E.

HK$4,963 total

includes taxes & fees

20 Oct - 21 Oct

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

20. Luxe Row Home Steps to USNA Gate 3!

Historic District

Christine A.

HK$9,895 total

includes taxes & fees

20 Oct - 21 Oct

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Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Everything was great. Staff was very helpful"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."

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