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Top Holiday Rentals in Chester

Room for an Island getaway

2.0 star property
10.0 out of 10, Exceptional, (1)
"Was a nice place for the night we were there. It had everything we needed for the night"
The price is £161
includes taxes & fees
30 Jun - 1 Jul
Room for an Island getaway

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

10.0 out of 10, Exceptional, (5)
"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 £334
includes taxes & fees
2 Jul - 3 Jul
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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

9.6 out of 10, Exceptional, (9)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is £255
includes taxes & fees
1 Jul - 2 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

#2 Egret Cottage Harris Cove

The price is £288
includes taxes & fees
24 Jul - 25 Jul
#2 Egret Cottage Harris Cove

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 £322
includes taxes & fees
26 Jun - 27 Jun
Bayside Cottage steps from Rock Hall Harbor

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (39)
"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 £226
includes taxes & fees
26 Jun - 27 Jun
BAYSIDE BUNGALOW

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

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is £242
includes taxes & fees
2 Jul - 3 Jul
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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 £239
includes taxes & fees
26 Jun - 27 Jun
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 £1,047
includes taxes & fees
21 Jul - 22 Jul
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 £949
includes taxes & fees
26 Jun - 27 Jun
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, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is £409
includes taxes & fees
27 Jun - 28 Jun
Charming Pet-Friendly Stay - Near Bay & Beaches.

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

10.0 out of 10, Exceptional, (1)
"The house is beautiful and on the water. Pool was great. Place was clean. Good communication from hosts. Lovely walking around the neighborhood. Short walk to views of the Bay and mouth of the Severn River. "
The price is £1,041
includes taxes & fees
7 Jul - 8 Jul
Oasis by the Bay - Waterfront Heated Pool Hot Tub!

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 £591
includes taxes & fees
2 Jul - 3 Jul
Charming Cottage with Hot Tub 1 Block from the Bay

Neptune by the Water

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 £451
includes taxes & fees
8 Jul - 9 Jul
Neptune by the Water

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
The price is £459
includes taxes & fees
21 Jul - 22 Jul
Charming Historic Row House in The Heart of Eastport's Horn Point

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 £479
includes taxes & fees
7 Jul - 8 Jul
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 £418
includes taxes & fees
1 Jul - 2 Jul
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 £353
includes taxes & fees
30 Jun - 1 Jul
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is £336
includes taxes & fees
7 Jul - 8 Jul
The Cottage

USNA Luxury Home, parking, pet friendly

10.0 out of 10, Exceptional, (7)
"Beautiful house in a great location to Main Street Annapolis. "
The price is £915
includes taxes & fees
8 Jul - 9 Jul
USNA Luxury Home, parking, pet friendly
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 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chester offers a balcony, a garden and a BBQ 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 that you can cook with friends or family.

How many holiday rentals will I find in Chester?

Choose from 12 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.