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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chesapeake Beach vacation rentals

Pool

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 CA $205
CA $652 total
includes taxes & fees
Oct 12 - Oct 13
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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $151
CA $494 total
includes taxes & fees
Nov 3 - Nov 4
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

3. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"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 CA $320
CA $618 total
includes taxes & fees
Oct 12 - Oct 13
Rose Haven Coastal Cottage
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

4. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is CA $169
CA $412 total
includes taxes & fees
Oct 12 - Oct 13
The Cozy Crab- Your Charming Haven in Lovely North Beach!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

5. 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, (38 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 CA $200
CA $643 total
includes taxes & fees
Nov 3 - Nov 4
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A house with a yellow door and a window with a lamp outside.

6. 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.
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Exterior

7. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $388
CA $653 total
includes taxes & fees
Oct 10 - Oct 11
Plum Point Cottage #17
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

8. 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 CA $330
CA $689 total
includes taxes & fees
Nov 4 - Nov 5
Sunset Cottage - West River Access and Views!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

9. 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 CA $256
CA $647 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in Deale located on Bay many amenities and great views
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

10. 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 CA $242
CA $411 total
includes taxes & fees
Oct 12 - Oct 13
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A deck with outdoor furniture, a red door, and a house with windows.

11. 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 $245
CA $541 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

12. 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 $167
CA $465 total
includes taxes & fees
Oct 19 - Oct 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lakeside view with chairs and a table, a rainbow, and trees.

13. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 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 CA $294
CA $510 total
includes taxes & fees
Oct 11 - Oct 12
Bright and airy waterfront getaway
A beach with chairs and a pier in the background.

14. 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 CA $294
CA $702 total
includes taxes & fees
Oct 20 - Oct 21
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $377
CA $1,049 total
includes taxes & fees
Oct 22 - Oct 23
Family Home on Mayo Peninsula | Deck | Sleeps 10
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

16. 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 CA $323
CA $856 total
includes taxes & fees
Nov 2 - Nov 3
Renovated Bungalow | Walk to Beach | Dog-Friendly
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

17. 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 CA $172
CA $370 total
includes taxes & fees
Oct 20 - Oct 21
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

18. 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 CA $457
CA $858 total
includes taxes & fees
Nov 9 - Nov 10
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Three birds perched on a wooden structure by the water.

19. 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)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is CA $1,137
CA $1,967 total
includes taxes & fees
Oct 11 - Oct 12
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a red roof, a brick chimney, and a small porch.

20. 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
8.0 out of 10, Very good, (5 reviews)
"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...
United States
Suzanne R.
The price is CA $1,024
CA $1,499 total
includes taxes & fees
Oct 11 - Oct 12
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
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

Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

10/10 Excellent
"Clean & comfy room. Nice staff."
Alicia 6-night trip
Posted 1 day ago
Residence Inn by Marriott Waldorf

Find out more about Chesapeake Beach

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesapeake Beach. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.