Chester Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Chester holiday rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (109 reviews)
"Every thing was great"
United States
lesia k.
The price is HK$775
HK$1,243 total
includes taxes & fees
29 Apr - 30 Apr
First Floor Studio Apartment in Historic Chestertown
Property grounds

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (28 reviews)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is HK$1,441
HK$2,756 total
includes taxes & fees
10 May - 11 May
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is HK$576
HK$1,962 total
includes taxes & fees
21 Apr - 22 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is HK$453
HK$1,799 total
includes taxes & fees
19 Apr - 20 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (19 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$923
HK$2,221 total
includes taxes & fees
19 Apr - 20 Apr
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Dining

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is HK$1,956
HK$3,276 total
includes taxes & fees
21 Apr - 22 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"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!"
United States
Dorothy R.
The price is HK$1,371
HK$2,848 total
includes taxes & fees
4 May - 5 May
Bayside Cottage steps from Rock Hall Harbor
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is HK$589
HK$2,475 total
includes taxes & fees
19 Apr - 20 Apr
Walk to Beach! King Bed & Free Beach Passes
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is HK$1,056
HK$2,516 total
includes taxes & fees
26 Apr - 27 Apr
Large 2 bedroom house with private parking in a nice neighborhood
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,409
HK$2,157 total
includes taxes & fees
1 May - 2 May
BAYSIDE BUNGALOW
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,349
HK$3,794 total
includes taxes & fees
20 Apr - 21 Apr
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is HK$1,174
HK$4,371 total
includes taxes & fees
20 Apr - 21 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,937
HK$3,644 total
includes taxes & fees
19 Apr - 20 Apr
Waterfront Oasis of Annapolis Star
Terrace/patio

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (8 reviews)
"Great place!"
United States
Chris A.
The price is HK$1,093
HK$2,825 total
includes taxes & fees
27 Apr - 28 Apr
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Outdoor dining

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is HK$775
HK$2,676 total
includes taxes & fees
20 Apr - 21 Apr
Waterfront Unit | Dock, Kayaks & SUPs Included
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$896
HK$3,340 total
includes taxes & fees
23 Apr - 24 Apr
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Property grounds

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is HK$1,423
HK$3,541 total
includes taxes & fees
19 Apr - 20 Apr
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Living area

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is HK$1,167
HK$4,545 total
includes taxes & fees
20 Apr - 21 Apr
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is HK$1,339
HK$2,929 total
includes taxes & fees
19 Apr - 20 Apr
Cozy 2br home w/ parking in downtown Annapolis
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is HK$978
HK$3,042 total
includes taxes & fees
6 May - 7 May
Pool Loft Suite | Bay Access & Beach Passes
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Everithing was so good , the room.so clean , the location was perfect"
Milagros 3-night trip
Posted 8 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
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  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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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?

Waterfront Sunset Bayview: sleeps 6: This highly rated holiday home rental in Chester is located on the waterfront, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable 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.

How many holiday rentals will I find in Chester?

Choose from 9 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 Northern Chesapeake Bay. Matapeake State Park and Chesapeake Bay Environmental Center 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.