Holiday Homes in Chester

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Our top choices for Chester holiday homes

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 NZ$696
includes taxes & fees
12 May - 13 May
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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, (44 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is NZ$563
includes taxes & fees
14 May - 15 May
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 NZ$652
includes taxes & fees
26 May - 27 May
Charming Coastal/Country Home w/3 Acres & Sauna!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$494
includes taxes & fees
12 May - 13 May
BAYSIDE BUNGALOW

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 NZ$650
includes taxes & fees
2 June - 3 June
Bayside Cottage steps from Rock Hall Harbor

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is NZ$516
includes taxes & fees
14 May - 15 May
Walk to Beach! King Bed & Free Beach Passes

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is NZ$879
includes taxes & fees
12 May - 13 May
Charming Pet-Friendly Stay - Near Bay & Beaches.

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, (40 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 NZ$560
includes taxes & fees
1 June - 2 June
Large 2 bedroom house with private parking in a nice neighborhood

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 NZ$807
includes taxes & fees
24 May - 25 May
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
9.0 out of 10, Wonderful, (7 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is NZ$588
includes taxes & fees
12 May - 13 May
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is NZ$1,209
includes taxes & fees
1 June - 2 June
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is NZ$882
includes taxes & fees
25 May - 26 May
Cute bungalow blocks to Stadium

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (3 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is NZ$826
includes taxes & fees
26 May - 27 May
Sunset Cottage - West River Access and Views!

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (11 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
Secluded Tiny Pool House -Private Pool -Self Check in

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (78 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is NZ$705
includes taxes & fees
25 May - 26 May
Cozy 2br home w/ parking in downtown Annapolis

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"Easy check in, always clean and we had a power outage and Andrea ho back to us immediately! Great kitchen and living area!"
United States
Regina L.
Charming Annapolis WaterVIEW Home

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is NZ$721
includes taxes & fees
12 May - 13 May
3-Bedroom Beach Home w/ Backyard

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$993
includes taxes & fees
26 May - 27 May
Annapolis Retreat - 7 mins from downtown Annapolis!

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.0 out of 10, Wonderful, (11 reviews)
"THE PERFECT WATERSIDE GETAWAY!!! The Hideaway Spot is a true GEM of a location/property for "
United States
Karen M.
The price is NZ$764
includes taxes & fees
12 May - 13 May
The Hideaway Spot- Waterfront w/ Dock on Long Cove

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, (33 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$1,202
includes taxes & fees
25 May - 26 May
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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

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Chester Holiday Homes information

Number of reviews
451
Accommodation
654 Holiday Homes
Lowest Price
NZ$494
Highest Price
NZ$1,209