A boat docked at a pier during twilight with a city skyline in the background.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chester vacation rentals

Interior

1. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is SAR 1,337
SAR 1,627 total
includes taxes & fees
31 Aug - 1 Sep
Family Retreat at Lansdowne Manor
Smart TV, books

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is SAR 845
SAR 1,326 total
includes taxes & fees
3 Sep - 4 Sep
Newly restored apartment in the heart of Chestertown
Property grounds

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (122 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is SAR 372
SAR 596 total
includes taxes & fees
3 Sep - 4 Sep
First Floor Studio Apartment in Historic Chestertown
Dining

4. 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 SAR 939
SAR 1,592 total
includes taxes & fees
1 Sep - 2 Sep
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Beach

5. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is SAR 442
SAR 1,081 total
includes taxes & fees
23 Aug - 24 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

6. 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 SAR 819
SAR 1,560 total
includes taxes & fees
21 Sep - 22 Sep
Bayside Cottage steps from Rock Hall Harbor
Exterior detail

7. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is SAR 751
SAR 1,185 total
includes taxes & fees
31 Aug - 1 Sep
BAYSIDE BUNGALOW
Exterior

8. 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!"
United States
Michelle P.
The price is SAR 542
SAR 1,287 total
includes taxes & fees
31 Aug - 1 Sep
Charming Coastal/Country Home w/3 Acres & Sauna!
Outdoor dining

9. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
The price is SAR 2,362
SAR 4,454 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Escape with Pool Nature Lover Paradise
Exterior

10. 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 parking
Stevensville
6.8 out of 10, (3 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."
United States
Anonymous traveler
The price is SAR 2,703
SAR 3,952 total
includes taxes & fees
3 Sep - 4 Sep
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Exterior

11. 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, (54 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 SAR 526
SAR 1,292 total
includes taxes & fees
30 Aug - 31 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

12. 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 SAR 3,192
SAR 5,430 total
includes taxes & fees
24 Aug - 25 Aug
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
On the beach, sun loungers, beach towels

13. 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, (76 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is SAR 3,192
SAR 5,430 total
includes taxes & fees
24 Aug - 25 Aug
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Outdoor dining

14. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (74 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is SAR 1,247
SAR 2,547 total
includes taxes & fees
14 Sep - 15 Sep
Charming Annapolis WaterVIEW Home
Beach nearby, sun loungers, beach towels

15. 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)
"The perfect off-season get-away! "
United States
Pamela B.
The price is SAR 1,217
SAR 2,440 total
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Coffee/tea maker, fridge, microwave, oven

16. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is SAR 909
SAR 2,659 total
includes taxes & fees
24 Aug - 25 Aug
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Property grounds

17. 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
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful property and very clean with full amenities. We had a wonderful day. Thank you for everything."
United States
David S.
The price is SAR 1,436
SAR 2,630 total
includes taxes & fees
23 Aug - 24 Aug
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Coffee/tea maker, fridge, microwave, oven

18. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 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 1,835 total
includes taxes & fees
23 Aug - 24 Aug
Pool Loft Suite | Bay Access & Beach Passes
Outdoor pool, a heated pool

19. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is SAR 727
SAR 1,488 total
includes taxes & fees
23 Aug - 24 Aug
Waterfront Oasis of Annapolis Star
Exterior detail

20. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is SAR 490
SAR 1,252 total
includes taxes & fees
3 Sep - 4 Sep
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"I reserve two rooms for me and my family. We had an amazing time and the temperature was perfect. After being outside at the beach all day. The bathrooms were small but clean and the areas were all clean a lot of fresh tiles and wash rags and the bed was also clean breakfast in the morning was very nice. They had a pancake maker cereal, and there was something for everybody, including eggs and sausage I would definitely recommend and come again easy check-in process Miss D made everything enjoyable and check out with smooth as well."
Noelia 1-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis

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 Sandy Point Beach 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.