A coastal town with a marina, a bridge, and a highway.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chester vacation rentals

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

1. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is SAR 315
SAR 1,062 total
includes taxes & fees
15 Nov - 16 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview
A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

2. 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"
United States
Michael V.
The price is SAR 450
SAR 1,232 total
includes taxes & fees
23 Nov - 24 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

3. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (35 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is SAR 477
SAR 1,064 total
includes taxes & fees
14 Nov - 15 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

4. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is SAR 723
SAR 1,731 total
includes taxes & fees
14 Nov - 15 Nov
Pool Loft Suite | Bay Access & Beach Passes
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

5. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is SAR 1,013
SAR 1,166 total
includes taxes & fees
26 Nov - 27 Nov
Family Friendly Cozy 3 Bedroom Duplex
A sandy beach with a boat docked on the left and calm water.

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, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is SAR 247
SAR 743 total
includes taxes & fees
15 Nov - 16 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

7. 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, (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. "
United States
Linda B.
The price is SAR 507
SAR 1,177 total
includes taxes & fees
15 Nov - 16 Nov
Large 2 bedroom house with private parking in a nice neighborhood
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

8. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is SAR 372
SAR 564 total
includes taxes & fees
16 Nov - 17 Nov
First Floor Studio Apartment in Historic Chestertown
A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

9. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
BAYSIDE BUNGALOW
A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.

10. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is SAR 999
SAR 1,377 total
includes taxes & fees
22 Nov - 23 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A sandy beach with lounge chairs and a small pond.

11. 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)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is SAR 777
SAR 1,771 total
includes taxes & fees
16 Nov - 17 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A wooden cabin with a glass door, a deck, and a dock extending into calm water.

12. Houseboat Suite for Two near Annapolis

Houseboat Suite for Two near Annapolis
Arnold
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveler
The price is SAR 525
SAR 1,339 total
includes taxes & fees
15 Nov - 16 Nov
Houseboat Suite for Two near Annapolis
A calm lake with boats docked, a sandy shore, and houses in the background.

13. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
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. "
United States
Diane D.
The price is SAR 723
SAR 1,992 total
includes taxes & fees
14 Nov - 15 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly
A white building with black shutters, a wooden door, and a number '53' on the wall.

14. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (16 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is SAR 875
SAR 1,515 total
includes taxes & fees
14 Nov - 15 Nov
18th Cent. Charm in Historic Downtown Annapolis
A beach with a wooden fence and a pier in the distance.

15. 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!"
United States
Sam C.
The price is SAR 2,623
SAR 4,651 total
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A house with a stone facade, a white door with a glass panel, and a porch with two potted plants.

16. 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 SAR 788
SAR 1,994 total
includes taxes & fees
30 Nov - 1 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is SAR 901
SAR 1,737 total
includes taxes & fees
13 Dec - 14 Dec
Cozy 2br home w/ parking in downtown Annapolis
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

18. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is SAR 1,182
SAR 2,178 total
includes taxes & fees
17 Nov - 18 Nov
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A spacious room with a large sliding glass door leading to a deck, a sofa, a chair, and a small table.

19. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit
Pasadena
10.0 out of 10, Exceptional, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is SAR 660
SAR 1,535 total
includes taxes & fees
15 Nov - 16 Nov
Bay Sunsets for Two • Rooftop Fire Pit
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

20. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is SAR 844
SAR 1,977 total
includes taxes & fees
14 Dec - 15 Dec
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"We stayed in a room with two queens and a balcony facing the water. Gorgeous view. Room was exceptionally clean, spacious and had everything we needed. Staff was very friendly when we arrived at check in, personable and informative. The breakfast buffet was massive, had many options. Next door to the hotel, was a delicious restaurant, the Fisherman's Inn. Will definitely stay again!"
Sally 1-night trip
Posted 13 hours ago
Hyatt Place Kent Narrows & Marina

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near well known sights in Chester, or you can go with a secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and seafood restaurants. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best vacation rentals that Chester has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental near Chester is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chester?

Choose from 8 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. Matapeake State Park and Eastern Neck National Wildlife Refuge are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.