Chesapeake Beach Holiday Rentals from NZ$488: Search Short-Term Rentals

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Our top choices for Chesapeake Beach holiday rentals

1. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Chesapeak beach

Ben W.

includes taxes & fees

2 Dec - 3 Dec

A cozy living room with a teal sofa, round coffee table, and ottomans. A large mirror and a potted plant are on the walls.

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

North Beach

Johanna S.

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

North Beach

James L.

includes taxes & fees

19 Nov - 20 Nov

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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

North Beach

Sarah

includes taxes & fees

19 Nov - 20 Nov

A house with a yellow door and a window with a lamp outside.

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

Deale

Maude H.

includes taxes & fees

15 Nov - 16 Nov

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

6. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

7. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

includes taxes & fees

1 Dec - 2 Dec

A deck with outdoor furniture, a red door, and a house with windows.

8. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"

Jenny A.

includes taxes & fees

16 Nov - 17 Nov

9. Plum Point Cottage #17

Huntingtown

includes taxes & fees

13 Nov - 14 Nov

A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

10. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick

Sean B.

includes taxes & fees

20 Nov - 21 Nov

Three Adirondack chairs facing a beach with a clear view of the ocean.

11. Plum Point Cottage #14

Huntingtown

Yonnick H.

includes taxes & fees

13 Nov - 14 Nov

12. Plum Point Cottage #15

Maryland

includes taxes & fees

13 Nov - 14 Nov

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

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

Benedict

ed r.

includes taxes & fees

14 Nov - 15 Nov

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

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

Stevensville

Anthony P.

includes taxes & fees

15 Nov - 16 Nov

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

Edgewater

Diane D.

includes taxes & fees

13 Nov - 14 Nov

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

16. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

includes taxes & fees

17 Nov - 18 Nov

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Edgewater

Kristin G.

includes taxes & fees

13 Nov - 14 Nov

A lakeside view with chairs and a table, a rainbow, and trees.

18. Bright and airy waterfront getaway

Benedict

George

includes taxes & fees

14 Nov - 15 Nov

A beach with chairs and a pier in the background.

19. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

includes taxes & fees

16 Nov - 17 Nov

A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

20. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

includes taxes & fees

13 Nov - 14 Nov

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Top Chesapeake Beach Hotel Reviews

Rod 'N' Reel Resort

8/10 Good

"I truly enjoyed my stay at Rod ’N’ Reel! The front desk staff were nice, but there's a little room for improvement when it comes to customer service. The smiles were a bit lacking, and the warm, welcoming energy wasn't quite what I'm accustomed to as a frequent traveler. However, the experience was much brighter throughout the property! A special shout-out to Brittany, Anthony, April, and the entire security team. They were welcoming, friendly, and brought great energy to the experience. As a travel agent, I would absolutely recommend this property to my clients. Overall, I had an enjoyable stay and would return! Sn: I left something behind and the staff reached out to me. I appreciate that."

SpringHill Suites by Marriott Annapolis

8/10 Good

"The staff was very helpful & accommodating when we expressed our concerns. We had booked this stay as an in between stop on our long vacation & mainly booked it because it had an indoor pool the kids could use for the few days in the middle. We also were unaware there is a parking fee of 8 dollars every night you stay. We did leave a night early simply because the pool was closed for the weekend. When we arrived it was closed & we were told it would be closed all weekend but was open around 9 at night & filled with people. It was open again when we walked by around 2pm the next day with people in it once again. So we got dressed & went down to get in & it was once again closed & we were told again it was closed all weekend for maintenance. After the disappointment from the kiddos & the extra money I paid for a pool specifically ( not to mention the nightly parking fee ) we decided to leave early & just continue our driving travels. The front desk was very understanding & kind. They also offered to refund me a night even though we hadn’t decided to leave until 2pm the day before checking out. So that was very nice & I know the inconveniences were not the responsibility of the staff! Over all it was a great hotel room, comfy beds, & very nice stuff. Only issues were the pool, the lack of information regarding it & the parking fee."

Springhill Suites by Marriott Prince Frederick

10/10 Excellent

"The only think I would change is the coffee to one of the more modern automatic types and maybe add flavored creamer. The room coffee maker is older and they only provide a powder packet. I brought my own but the hotel was nice and I would sty again."

Find out more about Chesapeake Beach

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesapeake Beach holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesapeake Beach. 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 Chesapeake Beach. 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 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 holiday 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 Chesapeake Beach short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Chesapeake Beach?

Yes, there are holiday rentals in Chesapeake Beach close to Chesapeake Beach Water Park, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chesapeake Beach has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Chesapeake Beach is located near the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chesapeake Beach?

With 8 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chesapeake Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake Beach. Holiday rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.

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Check prices for these dates

Our top choices for Chesapeake Beach holiday rentals

1. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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

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

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

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

6. 3-bedroom house in Deale located on Bay many amenities and great views

7. Sunset Cottage - West River Access and Views!

8. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

9. Plum Point Cottage #17

10. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

11. Plum Point Cottage #14

12. Plum Point Cottage #15

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

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

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

16. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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

18. Bright and airy waterfront getaway

19. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

20. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Find holiday rentals that suit your style

Top Chesapeake Beach Hotel Reviews

Rod 'N' Reel Resort

Econo Lodge Andrews Air Force Base

Hilton Garden Inn Solomons

Candlewood Suites Annapolis by IHG

Towneplace Suites by Marriott Clinton at Joint Base Andrews

The Wildset

Courtyard Marriott Waldorf

SpringHill Suites by Marriott Annapolis

Springhill Suites by Marriott Prince Frederick

Find out more about Chesapeake Beach

Frequently asked questions

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