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Chester Holiday Rentals

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Holiday Rentals in Chester

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (19)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is AU$1,181
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is AU$682
includes taxes & fees
29 July - 30 July
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is AU$1,372
includes taxes & fees
3 Aug - 4 Aug
Gorgeous Creek Side Ranch-Style Estate With Dock

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is AU$650
includes taxes & fees
25 July - 26 July
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is AU$651
includes taxes & fees
27 July - 28 July
Bayside Cottage steps from Rock Hall Harbor

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (42)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AU$459
includes taxes & fees
29 July - 30 July
BAYSIDE BUNGALOW

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is AU$506
includes taxes & fees
3 Aug - 4 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$452
includes taxes & fees
27 July - 28 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is AU$2,135
includes taxes & fees
29 July - 30 July
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is AU$2,062
includes taxes & fees
29 July - 30 July
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (2)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (51)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
The price is AU$1,382
includes taxes & fees
20 Aug - 21 Aug
Charming Annapolis WaterVIEW Home

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$1,268
includes taxes & fees
18 Aug - 19 Aug
Charming Cottage with Hot Tub 1 Block from the Bay

Neptune by the Water - Pet Friendly Fenced Yard

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is AU$770
includes taxes & fees
29 July - 30 July
Neptune by the Water - Pet Friendly Fenced Yard

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is AU$937
includes taxes & fees
29 July - 30 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is AU$961
includes taxes & fees
5 Aug - 6 Aug
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is AU$728
includes taxes & fees
31 July - 1 Aug
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AU$691
includes taxes & fees
4 Aug - 5 Aug
The Cottage

USNA Luxury Home, parking, pet friendly

10.0 out of 10, Exceptional, (8)
"Beautiful house in a great location to Main Street Annapolis. "
The price is AU$1,403
includes taxes & fees
29 July - 30 July
USNA Luxury Home, parking, pet friendly

Historic Row Home 1 Block from Gate 1 at USNA!

The price is AU$1,018
includes taxes & fees
28 July - 29 July
Historic Row Home 1 Block from Gate 1 at USNA!
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

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chester has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chester is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Chester?

Choose from 15 Expedia holiday rentals in Chester for a memorable holiday.

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 wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips or small group gatherings.