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Our top choices for Chester vacation homes
1. Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
Michelle P.
The price is AED 407
AED 1,094 total
includes taxes & fees
2 Sep - 3 Sep
2. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
Dawn G.
The price is AED 309
AED 1,008 total
includes taxes & fees
1 Sep - 2 Sep
3. 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, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
Robin
The price is AED 918
AED 1,557 total
includes taxes & fees
1 Sep - 2 Sep
4. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
Diane V.
The price is AED 735
AED 1,159 total
includes taxes & fees
1 Sep - 2 Sep
5. Large 2 bedroom house with private parking in a nice neighborhood
Large 2 bedroom house with private parking in a nice neighborhoodArnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
Linda B.
The price is AED 512
AED 1,242 total
includes taxes & fees
1 Sep - 2 Sep
6. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach AccessShady Side
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
Joshua T.
The price is AED 251
AED 902 total
includes taxes & fees
1 Sep - 2 Sep
7. Cute, Cozy 2-bedroom house near Annapolis with water access
Cute, Cozy 2-bedroom house near Annapolis with water accessHerald Harbor
9.6 out of 10, Exceptional, (20 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
Taylor C.
The price is AED 314
AED 865 total
includes taxes & fees
2 Sep - 3 Sep
8. Bayside Cottage steps from Rock Hall Harbor
Bayside Cottage steps from Rock Hall HarborRock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
Adam S.
The price is AED 790
AED 1,515 total
includes taxes & fees
29 Sep - 30 Sep
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
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
