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Whitehall Holiday Rentals

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Our top choices for Whitehall holiday rentals

1. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is NZ$266
includes taxes & fees
16 Sept - 17 Sept
Pet-Friendly Pond Cottage • Nature Escape Near Beaches

2. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is NZ$424
includes taxes & fees
24 Aug - 25 Aug
Sailwinds Loft at Cambridge Creek

3. Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is NZ$435
includes taxes & fees
20 Aug - 21 Aug
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

4. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is NZ$868
includes taxes & fees
8 Sept - 9 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

5. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (14 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is NZ$1,159
includes taxes & fees
20 Aug - 21 Aug
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

6. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is NZ$877
includes taxes & fees
26 Aug - 27 Aug
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

7. Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (12 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is NZ$2,024
includes taxes & fees
16 Sept - 17 Sept
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

8. Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is NZ$789
includes taxes & fees
30 Aug - 31 Aug
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

9. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (64 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is NZ$467
includes taxes & fees
23 Aug - 24 Aug
Waterfront Getaway with Dock

10. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (34 reviews)
"Really comfortable house, plenty of space. Lovely surroundings for a low-key quiet getaway. *Note, the nearby general store has closed permanently as of 30Apr2026"
United States
Rochelle K.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

11. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is NZ$812
includes taxes & fees
8 Sept - 9 Sept
Sunset Breezes - quiet waterfront retreat

12. 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, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is NZ$1,031
includes taxes & fees
2 Sept - 3 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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 Whitehall Hotel Reviews

Find out more about Whitehall

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 Whitehall 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 Whitehall. 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 Whitehall. Seeing all the best attractions is bound to make you fall in love with Whitehall. 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 Whitehall short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Whitehall?

Yes, there are holiday rentals close to the most popular sights in Whitehall, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Whitehall has to offer?

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels: This holiday home rental outside of Whitehall offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Whitehall?

Explore the area and family-friendly sights such as Easton Cycle and Sport, or get out into nature at a spot like Long Wharf Park. Choptank River Lighthouse and Gerry Boyle Park at Great Marsh are a couple of places you'll find in the wider area.

What are holiday rentals like in Whitehall?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Whitehall. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for small groups.