Chester Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Vacation Rentals in Chester
![Caribbean Pool Home <1 mile from Matapeake Beach!](https://images.trvl-media.com/lodging/104000000/103440000/103432600/103432552/0d2c1b6b_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Caribbean Pool Home <1 mile from Matapeake Beach!
The price is $467 per night
$467
per night
Jun 30 - Jul 1
When you stay at this vacation home in Stevensville, you'll be near the beach and 7 minutes by foot from Matapeake State Park.
Pool
Kitchen
![Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/d8a574c5_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 10-minute drive of Sandy Point State Park and Chesapeake Bay Bridge.
Pool
Hot Tub
![BAYSIDE BUNGALOW](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/fc1adaf1_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
BAYSIDE BUNGALOW
The price is $175 per night
$175
per night
Jun 29 - Jun 30
Located in Rock Hall, this vacation home is within a 15-minute walk of Ferry Park and Waterman’s Museum.
Free WiFi
Air conditioning
![Miller's Cottage](https://images.trvl-media.com/lodging/60000000/59010000/59007200/59007108/06ed591f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Miller's Cottage
Located in Edgemere, this vacation home is within a 5-minute drive of North Point State Park and Patapsco River.
Kitchen
Washer
![Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport](https://images.trvl-media.com/lodging/86000000/85950000/85941000/85940932/c07a4288_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
A stay at this vacation home places you in the heart of Severna Park, a 2-minute drive from B&A Trail and 9 minutes from Chase Brexton Health Care - Glen Burnie Center.
Kitchen
Washer
![Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium](https://images.trvl-media.com/lodging/105000000/104820000/104817800/104817733/f2ec14a4_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
The price is $239 per night
$239
per night
Jun 30 - Jul 1
With a stay at this vacation home, you'll be centrally located in Annapolis, a 3-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.
Kitchen
Washer
![Pool and Bay Views on wrap around deck in Kent Island](https://images.trvl-media.com/lodging/64000000/63510000/63505500/63505478/902d890f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Pool and Bay Views on wrap around deck in Kent Island
With a stay at this vacation home in Stevensville, you'll be within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.
Pool
Kitchen
![A waterfront gem with dock, kayaks great water views. Sleeps up to 12.](https://images.trvl-media.com/lodging/95000000/94840000/94839700/94839681/29cc8f41_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Kitchen
Washer
![Recently Renovated Annapolis Home - Conveniently Located](https://images.trvl-media.com/lodging/75000000/74250000/74249000/74248912/de36f433_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Recently Renovated Annapolis Home - Conveniently Located
With a stay at this vacation home, you'll be centrally located in Annapolis, a 3-minute drive from U.S. Naval Academy and 13 minutes from Sandy Point State Park.
Kitchen
Washer
![Cozy and peaceful BASEMENT in a house, close to different restaurants and a park](https://images.trvl-media.com/lodging/100000000/100000000/99994700/99994635/603d8795_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
The price is $78 per night
$78
per night
Jul 4 - Jul 5
With a stay at this vacation home in Pasadena, you'll be within a 5-minute drive of Compass Pointe Golf Courses and Fort Smallwood Park.
Washer
Dryer
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.
Chester Vacation Rentals essential information
Accommodation | 594 Vacation Rentals |
---|---|
Lowest Price | $78 |
Highest Price | $467 |
Popular accommodation | Caribbean Pool Home <1 mile from Matapeake Beach!, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, BAYSIDE BUNGALOW, Miller's Cottage, Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport, Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium, Pool and Bay Views on wrap around deck in Kent Island, A waterfront gem with dock, kayaks great water views. Sleeps up to 12., Recently Renovated Annapolis Home - Conveniently Located, Cozy and peaceful BASEMENT in a house, close to different restaurants and a park, Pet Friendly - Stone's throw from Annapolis City Dock with private back patio, Cozy suite Located in Presidents Hill |