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Compare Vacation Homes in Chester with updated reviews, rates, and availability.

Caribbean Pool Home <1 mile from Matapeake Beach!
4 bedrooms, desk, iron/ironing board, travel crib
Caribbean Pool Home <1 mile from Matapeake Beach!
10.0 out of 10, Exceptional, (1)
"The house was exactly as promised! We were very happy with the accommodations!"
The price is $470
$1,072 total
includes taxes & fees
Jun 23 - Jun 24
Caribbean Pool Home <1 mile from Matapeake Beach!
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, (5)
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Historic Annapolis Home!
Fridge, microwave, oven, stovetop
Historic Annapolis Home!
10.0 out of 10, Exceptional, (1)
"Great location for commissioning week! The house was cute, cozy, clean and we loved it!"
Historic Annapolis Home!
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Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (181)
"Prime location!"
Directly Across from Gate One & Steps from the Waterfront
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Property grounds
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
10.0 out of 10, Exceptional, (3)
"Beautiful property, both inside and out, which was comfortable for two families with numerous children. Hosts were kind enough to make amenities beyond the usual available, including yard games, fishing rods, fire pit, and bicycles. We were VERY comfortable throughout our stay and were appreciative of everything this charming house had to offer. Three out of the four bedrooms had enough space for a crib, and the last still had a queen size bed that fit perfectly in the space with room to move...
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (27)
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Historic Firehouse fully renovated with Parking and Pet Friendly
Property grounds
Historic Firehouse fully renovated with Parking and Pet Friendly
10.0 out of 10, Exceptional, (51)
"I stayed at this property for a family wedding this last weekend with 5 other adult family members. The original spot we booked fell through last second and I found this unique property. It fit our needs perfectly. There was plenty of space. Everything was clean. The outdoor sitting areas were an added bonus. Plenty of parking. And the location in relation to downtown were perfect. I’d definitely stay here again."
Historic Firehouse fully renovated with Parking and Pet Friendly
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Property grounds
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
9.8 out of 10, Exceptional, (7)
"Super close to all downtown amenities. Would definitely return."
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Cozy suite Located in Presidents Hill
Interior
Cozy suite Located in Presidents Hill
10.0 out of 10, Exceptional, (8)
"Loved the small touches of cookies, snacks, gifts- all super welcoming and homey- thank you!"
The price is $366
$575 total
includes taxes & fees
Jun 16 - Jun 17
Cozy suite Located in Presidents Hill
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Fridge, microwave, oven, stovetop
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
The price is $239
$467 total
includes taxes & fees
Jun 16 - Jun 17
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (15)
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (18)
"This is a excellent cottage for a short getaway. As the listing states, the cottage is small so only big enough for 1-2 people. There is a nice refrigerator and microwave to heat things up but no facilities for cooking. Paul and Chris are very friendly and helpful. Their dog Vinny is also friendly. We came for a triathlon and the porch was a covered so we could keep our bikes there. The sauna was also great to use after our triathlon."
The price is $175
$272 total
includes taxes & fees
Jun 16 - Jun 17
BAYSIDE BUNGALOW
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
10.0 out of 10, Exceptional, (7)
"I couldn’t have found a better place this gave us a great nights rest every night. We had a lot planned and all turned out great. Our first night we didn’t stop to eat so we asked Jimmy where we can go he directed us to a great Chinese restaurant. We were right smack in the middle of all our plans. Friday night An Inner Harbor Dinner Cruise. Saturday night a Kenny Chesney Concert. Sunday a Bowie Baysocks game and Monday on our way home stopped at the B&O Railroad Museum. What a great time thank...
The price is $78
$121 total
includes taxes & fees
Jun 16 - Jun 17
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Jackson's Bunker in Eastport with fenced-in backyard
Property grounds
Jackson's Bunker in Eastport with fenced-in backyard
10.0 out of 10, Exceptional, (7)
"This home has a fenced-in backyard and is dog-friendly, making it a good spot for visiting Annapolis with a dog in tow. Along with being a five-minute drive to downtown Annapolis, this home is also close to Quiet Waters Park. Sean is terrific at communicating; the complimentary wine and coffee were appreciated!"
Jackson's Bunker in Eastport with fenced-in backyard
Entire Townhouse in Rock Hall
Fridge, microwave, oven, stovetop
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (16)
"Clean, bright, beautiful. Plenty of room for 6 of us to stay. Great location. Nice place for walking. Close and convenient to town and the harbor. Highly recommended."
Entire Townhouse in Rock Hall
Miller's Cottage
Combined shower/tub, hair dryer, toilet paper
Miller's Cottage
10.0 out of 10, Exceptional, (24)
"We are from NY and had a major surgery at Johns Hopkins. Miller's Cottage was the perfect location for us to spend the week post-op prior to returning home to NY. Miller's cottage was clean, comfortable and very well equipped. There was outside seating which allowed us to enjoy the fresh air while recovering."
Miller's Cottage
Eastport Cottage .5 mi from Downtown Annapolis
Exterior
Eastport Cottage .5 mi from Downtown Annapolis
10.0 out of 10, Exceptional, (52)
"Small but mighty Eastport house, super convenient to all thing Annapolis. Clean, equipped, comfortable. Mark is great at all things communication. Stay here….just not on the dates that I need it!"
Eastport Cottage .5 mi from Downtown Annapolis
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Property grounds
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
10.0 out of 10, Exceptional, (7)
"We had a family reunion in the area and my brother, and I and our spouses spent 4 nights. It was a perfect fit for our needs. Extremely clean and well appointed. Even the coffee was great. Thanks so much."
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
Fridge, microwave, oven, stovetop
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
10.0 out of 10, Exceptional, (9)
"Our stay in Annapolis was a short and sweet 3-day visit for a wedding--my original focus was to have enough space for everyone to get ready without waiting in line. The property provided so much more than enough room. The entire house was very clean, well-appointed, and smartly laid out. The kitchen was stock with a wide range of food to get the weekend started off without the need to spend hours in the local grocery store. Throw in a great ping-pong table to make it even more fun. My only two...
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
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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.

Other property types in Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Interior
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (6)
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
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, (5)
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cozy place close to the city dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (55)
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city dock
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 Homes information

Number of reviews
Accommodation
 Vacation Homes
Lowest Price
Highest Price

Recent reviews of Chester hotels
Expedia verified reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

5/5 Excellent
10/10... highly recommend!
"My stay was amazing... the fresh cookies were great. Also, the best complimentary breakfast I have ever had at a hotel. Great location near a mall. Nice quiet and clean!"
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD