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Chester Vacation Rentals

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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, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $170
CA $448 total
includes taxes & fees
Sep 17 - Sep 18
Charming Coastal/Country Home w/3 Acres & Sauna!

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."
United States
Dawn G.
The price is CA $153
CA $426 total
includes taxes & fees
Sep 16 - Sep 17
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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. "
United States
Robin
The price is CA $345
CA $582 total
includes taxes & fees
Sep 14 - Sep 15
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

4. 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)
"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. "
United States
Linda B.
The price is CA $193
CA $463 total
includes taxes & fees
Sep 23 - Sep 24
Large 2 bedroom house with private parking in a nice neighborhood

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $248
CA $401 total
includes taxes & fees
Sep 11 - Sep 12
BAYSIDE BUNGALOW

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (22 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!"
United States
Taylor C.
The price is CA $119
CA $324 total
includes taxes & fees
Oct 6 - Oct 7
Cute, Cozy 2-bedroom house near Annapolis with water access

7. 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, (19 reviews)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is CA $248
CA $632 total
includes taxes & fees
Sep 14 - Sep 15
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

8. 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 $317
CA $839 total
includes taxes & fees
Oct 6 - Oct 7
Annapolis Retreat - 7 mins from downtown Annapolis!

9. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is CA $333
CA $786 total
includes taxes & fees
Sep 14 - Sep 15
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

10. 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 Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $101
CA $344 total
includes taxes & fees
Sep 21 - Sep 22
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

11. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is CA $340
CA $892 total
includes taxes & fees
Sep 13 - Sep 14
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

12. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (74 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is CA $1,035
CA $1,828 total
includes taxes & fees
Sep 15 - Sep 16
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

13. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is CA $265
CA $776 total
includes taxes & fees
Sep 14 - Sep 15
Historic Row Home | Hot Tub - 1 Block from Gate 1!

14. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is CA $364
CA $790 total
includes taxes & fees
Sep 15 - Sep 16
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

15. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is CA $295
CA $601 total
includes taxes & fees
Sep 23 - Sep 24
Cozy 2br home w/ parking in downtown Annapolis

16. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is CA $361
CA $1,001 total
includes taxes & fees
Sep 14 - Sep 15
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

17. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is CA $294
CA $565 total
includes taxes & fees
Sep 29 - Sep 30
Bayside Cottage steps from Rock Hall Harbor

18. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is CA $1,115
CA $1,928 total
includes taxes & fees
Sep 23 - Sep 24
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

19. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
"This property was an up and down property for us. The ups: check in process was flawless; cleanliness was as good as an old house can be; and the location was superb. The downs: they say it can sleep ten. Well ten people might sleep but they can’t do much else. There are two baths and the kitchen was fine and although adequate to work with. But there are only four wine glasses and barely five people can sit at the dining room table. So if ten people sleep - they wake up and there are enough...
United States
DEAN F.
The price is CA $256
CA $776 total
includes taxes & fees
Sep 14 - Sep 15
Historic Row Home in Downtown Annapolis

20. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $334
CA $976 total
includes taxes & fees
Sep 12 - Sep 13
Family Home on Mayo Peninsula | Deck | Sleeps 10
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 Vacation Homes information

Number of reviews
429
Accommodation
616 Vacation Homes
Lowest Price
CA $324
Highest Price
CA $1,928

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