Chester Vacation Rentals

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Our top choices for Chester vacation 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, (14 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. "
United States
Robin
The price is CA $352
CA $595 total
includes taxes & fees
Jun 26 - Jun 27
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is CA $245
CA $548 total
includes taxes & fees
Jun 30 - Jul 1
Charming Coastal/Country Home w/3 Acres & Sauna!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (55 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is CA $254
CA $389 total
includes taxes & fees
Jun 24 - Jun 25
BAYSIDE BUNGALOW

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, (46 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 CA $223
CA $519 total
includes taxes & fees
Jun 30 - Jul 1
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is CA $277
CA $544 total
includes taxes & fees
Jul 14 - Jul 15
Bayside Cottage steps from Rock Hall Harbor

Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (35 reviews)
"Place was very accommodating for our needs!"
United States
Antonia P.
Idyllic Pasadena Retreat with Garden + Hot Tub!

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)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is CA $269
CA $567 total
includes taxes & fees
Jul 20 - Jul 21
Large 2 bedroom house with private parking in a nice neighborhood

Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.2 out of 10, Wonderful, (10 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is CA $121
CA $329 total
includes taxes & fees
Jun 21 - Jun 22
Cute, Cozy 2-bedroom house near Annapolis with water access

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 CA $431
CA $1,004 total
includes taxes & fees
Jul 13 - Jul 14
Annapolis Retreat - 7 mins from downtown Annapolis!

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (21 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is CA $186
CA $554 total
includes taxes & fees
Jun 24 - Jun 25
Walk to Beach! King Bed & Free Beach Passes

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, (15 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $543
CA $1,027 total
includes taxes & fees
Jul 14 - Jul 15
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $457
CA $843 total
includes taxes & fees
Jun 22 - Jun 23
Sunset Cottage - West River Access and Views!

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The view was incredible! So magical. My daughters and I watched the sunrise over the bay every morning from the living room. On our last morning there was a family of deer grazing as we watched - it was so beautiful! The master bathroom is amazing. It was the perfect spot for family to gather for brunch before a wedding! "
United States
Lia D.
The price is CA $678
CA $1,231 total
includes taxes & fees
Jul 13 - Jul 14
Charming Annapolis WaterVIEW Home

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 CA $341
CA $977 total
includes taxes & fees
Jun 21 - Jun 22
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is CA $126
CA $484 total
includes taxes & fees
Jun 23 - Jun 24
3-bedroom house in Deale located on Bay many amenities and great views

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is CA $396
CA $792 total
includes taxes & fees
Jun 23 - Jun 24
3-Bedroom Beach Home w/ Backyard

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.4 out of 10, Very good, (12 reviews)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
United States
Stephen R A.
The price is CA $298
CA $388 total
includes taxes & fees
Jul 1 - Jul 2
Secluded Tiny Pool House -Private Pool -Self Check in

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.2 out of 10, Wonderful, (13 reviews)
"THE PERFECT WATERSIDE GETAWAY!!! The Hideaway Spot is a true GEM of a location/property for "
United States
Karen M.
The price is CA $387
CA $804 total
includes taxes & fees
Jun 21 - Jun 22
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (7 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is CA $350
CA $890 total
includes taxes & fees
Jul 8 - Jul 9
Renovated Bungalow | Walk to Beach | Dog-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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Top Chester Hotel Reviews

Find out more about Chester

Chester Vacation Homes information

Number of reviews
14,972
Accommodation
658 Vacation Homes
Lowest Price
CA $126
Highest Price
CA $359

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