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Chester Vacation Rentals

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Check prices for these dates

Tonight
Jun 20 - Jun 21
Tomorrow
Jun 21 - Jun 22
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Chester

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Marina

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (52)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (28)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (210)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Interior

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (45)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Cass-N-Reel Luxury Houseboat
Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (28)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Marina

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (222)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Circa 1700 Chesapeake Colonial home on the National Register.
Exterior

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (53)
"Great and comfortable stay! Beautiful historic house and property Owners were so friendly and helpful"
Circa 1700 Chesapeake Colonial home on the National Register.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (36)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is ￥22,762
￥53,584 total
includes taxes & fees
Jun 30 - Jul 1
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Blue Crab Beach House - Free beach passes
Beach nearby, sun loungers, beach towels

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (58)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
Private Cottage on gated estate
Property grounds

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (181)
"A clean, comfortable getaway house, walking distance to St. Michaels and marinas, and well appointed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is ￥32,008
￥69,163 total
includes taxes & fees
Jul 7 - Jul 8
The Cottage
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.8 out of 10, Exceptional, (8)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is ￥157,420
￥242,983 total
includes taxes & fees
Jun 23 - Jun 24
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Dining

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (35)
"Was a great vacation hope to come back next year!"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (40)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Secluded Tiny House -Private Pool -Self Check in
Outdoor pool

Secluded Tiny House -Private Pool -Self Check in

9.8 out of 10, Exceptional, (6)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
The price is ￥24,006
￥30,684 total
includes taxes & fees
Jul 7 - Jul 8
Secluded Tiny House -Private Pool -Self Check in
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (4)
"A few local spots to eat were great in the morning especially the Tighlman Market! Market has all you need to stock up with groceries and is just 2 minutes from the house."
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is ￥39,282
￥71,982 total
includes taxes & fees
Jun 23 - Jun 24
Waterfront Oasis of Annapolis Star
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Dining

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (102)
"Had a wonderful, peaceful stay."
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
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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Frequently asked questions

Can I find vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near well known sights in Chester, or you can go with a secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and seafood restaurants. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best vacation rentals that Chester has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental near Chester offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Chester?

Choose from 11 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Chesapeake Bay Environmental Center. Matapeake State Park and Love Point State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.