Holiday Homes in Chester
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Our top choices for Chester holiday 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, (50 reviews)
"Great stay"
Michael V.
The price is €290
includes taxes & fees
23 Nov - 24 Nov
2. Relax on Kent Island in 4 Bedroom Home w/Waterview
Relax on Kent Island in 4 Bedroom Home w/WaterviewStevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
Anthony P.
The price is €263
includes taxes & fees
15 Nov - 16 Nov
3. Family Friendly Cozy 3 Bedroom Duplex
Family Friendly Cozy 3 Bedroom DuplexGrasonville
The price is €275
includes taxes & fees
24 Nov - 25 Nov
4. 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, (44 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 €309
includes taxes & fees
10 Dec - 11 Dec
5. 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, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
Sam C.
The price is €1,131
includes taxes & fees
6 Dec - 7 Dec
6. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community BeachArundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
Ryan C.
The price is €426
includes taxes & fees
16 Nov - 17 Nov
7. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
Diane V.
8. Cute, Cozy 2-bedroom house near Annapolis with water access
Cute, Cozy 2-bedroom house near Annapolis with water accessHerald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
Guillaume P.
The price is €181
includes taxes & fees
15 Nov - 16 Nov
9. 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!"
Paul C.
The price is €631
includes taxes & fees
24 Nov - 25 Nov
10. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
David R.
11. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 MinCape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
Jennifer H.
The price is €534
includes taxes & fees
17 Nov - 18 Nov
12. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and DowntownHomewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
Dan B.
13. Cozy 2br home w/ parking in downtown Annapolis
Cozy 2br home w/ parking in downtown AnnapolisHistoric District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
Nancy N.
The price is €460
includes taxes & fees
24 Nov - 25 Nov
14. 5 bedroom house with EV charger Near Downtown Annapolis
5 bedroom house with EV charger Near Downtown AnnapolisEastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
Jacob V.
The price is €538
includes taxes & fees
15 Nov - 16 Nov
15. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parkingStevensville
8.6 out of 10, Excellent, (7 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
Anonymous traveller
The price is €893
includes taxes & fees
13 Nov - 14 Nov
16. Renovated Bungalow | Walk to Beach | Dog-Friendly
Renovated Bungalow | Walk to Beach | Dog-FriendlyEdgewater
9.6 out of 10, Exceptional, (14 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
Diane D.
17. Cute bungalow blocks to Stadium
Cute bungalow blocks to StadiumAdmiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
Heather B.
The price is €520
includes taxes & fees
30 Nov - 1 Dec
18. The Harness Creek Retreat in Annapolis
The Harness Creek Retreat in AnnapolisHillsmere
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay! The property was beautiful, exceptionally clean, and in a perfect location for enjoying everything Annapolis has to offer. The beds were very comfortable, and the home had wonderful amenities that made our stay even more enjoyable. We couldn’t have asked for a better place to stay and would absolutely return. Highly recommend!"
Dayna A.
The price is €384
includes taxes & fees
12 Nov - 13 Nov
19. Family Home on Mayo Peninsula | Deck | Sleeps 10
Family Home on Mayo Peninsula | Deck | Sleeps 10Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
Kristin G.
The price is €601
includes taxes & fees
12 Nov - 13 Nov
20. Fabulous 5-bedroom house with AC in charming Annapolis
Fabulous 5-bedroom house with AC in charming AnnapolisAnnapolis
8.6 out of 10, Excellent, (17 reviews)
"Very nice home. Definitely recommend!"
Bob H.
The price is €376
includes taxes & fees
17 Nov - 18 Nov
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
10/10 Excellent
Find out more about Chester
Chester Holiday Homes information
Number of reviews | 494 |
|---|---|
Accommodation | 611 Holiday Homes |
Lowest Price | €181 |
Highest Price | €1,131 |