A harbor with boats docked, a pier, and a row of houses along the water.

Chesapeake Beach Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chesapeake Beach vacation rentals

1. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ￥24,848
￥74,458 total
includes taxes & fees
Oct 20 - Oct 21
Family Beach House: Spacious Deck, Grill & Views
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥13,926
￥50,739 total
includes taxes & fees
Sep 29 - Sep 30
Beachside Oasis with Beach Passes & King Suite by A Haven Away
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is ￥15,151
￥61,671 total
includes taxes & fees
Sep 29 - Sep 30
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

4. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is ￥35,851
￥68,871 total
includes taxes & fees
Sep 28 - Sep 29
Rose Haven Coastal Cottage
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

5. 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 ￥35,710
￥78,762 total
includes taxes & fees
Sep 30 - Oct 1
3-bedroom house in Deale located on Bay many amenities and great views
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

6. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is ￥42,905
￥72,073 total
includes taxes & fees
Sep 26 - Sep 27
Plum Point Cottage #17
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

7. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is ￥26,767
￥45,204 total
includes taxes & fees
Sep 27 - Sep 28
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

8. 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 ￥14,989
￥46,679 total
includes taxes & fees
Sep 28 - Sep 29
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

9. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is ￥19,130
￥40,806 total
includes taxes & fees
Oct 7 - Oct 8
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A deck with outdoor furniture, a red door, and a house with windows.

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 ￥28,624
￥61,709 total
includes taxes & fees
Sep 30 - Oct 1
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

11. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is ￥48,905
￥90,885 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Cottage - West River Access and Views!
A lakeside view with chairs and a table, a rainbow, and trees.

12. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is ￥36,214
￥60,250 total
includes taxes & fees
Sep 29 - Sep 30
Bright and airy waterfront getaway
A beach with chairs and a pier in the background.

13. 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 ￥34,718
￥80,144 total
includes taxes & fees
Sep 28 - Sep 29
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A house with a brick exterior, a front porch with a bench, and hanging flower baskets.

14. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is ￥42,512
￥70,362 total
includes taxes & fees
Sep 30 - Oct 1
The Harness Creek Retreat in Annapolis
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 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 ￥38,733
￥98,183 total
includes taxes & fees
Oct 20 - Oct 21
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

16. 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)
The price is ￥45,346
￥120,799 total
includes taxes & fees
Oct 6 - Oct 7
Family Home on Mayo Peninsula | Deck | Sleeps 10
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

17. 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 ￥31,333
￥88,849 total
includes taxes & fees
Oct 20 - Oct 21
Annapolis Retreat - 7 mins from downtown Annapolis!

18. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
The price is ￥24,798
￥36,235 total
includes taxes & fees
Sep 28 - Sep 29
Just a getaway piece of property
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

19. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is ￥52,218
￥97,409 total
includes taxes & fees
Oct 7 - Oct 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ￥30,150
￥80,321 total
includes taxes & fees
Oct 12 - Oct 13
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 Chesapeake Beach Hotel Reviews

Spark by Hilton Waldorf

Spark by Hilton Waldorf

8/10 Good
"Overall quite clean and reasonably well maintained."
Zheng 2-night trip
Posted 12 hours ago
Spark by Hilton Waldorf

Find out more about Chesapeake Beach

Search for holiday rentals in Chesapeake Beach on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake Beach using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake Beach
  • Use the map to find apartments and other holiday homes in the Chesapeake Beach neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake Beach while they last

Look no further and take a look at our great range of rental properties in Chesapeake Beach!

Frequently asked questions

Can I find a vacation rental in Chesapeake Beach?

Yes, you can find vacation rentals in Chesapeake Beach near Chesapeake Beach Water Park, or you can select a more remote option if you're looking for extra privacy while you relax. Discover why Chesapeake Beach is known for its spas and beaches. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best vacation home rentals that Chesapeake Beach has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental near Chesapeake Beach 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 Chesapeake Beach?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Chesapeake Beach stay.

What’s there to see and do in Chesapeake Beach?

Family-friendly attractions include Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, whereas Breezy Point Beach and Northern Chesapeake Bay are a couple of great spots to enjoy the outdoors. Other places in town to visit include Rod n Reel Charter Fishing and Chesapeake Bay.

What’s a vacation rental in Chesapeake Beach like?

Vacation rentals are privately owned properties you can book for several days or longer in Chesapeake Beach. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.