Whitehall Holiday Rentals

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Holiday Rentals in Whitehall

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$602
includes taxes & fees
29 Sept - 30 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (26)
"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Sailwinds Loft at Cambridge Creek

10.0 out of 10, Exceptional, (15)
"The location and apartment were perfect. "
The price is NZ$436
includes taxes & fees
8 Oct - 9 Oct
Sailwinds Loft at Cambridge Creek

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (11)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (257)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Station House East: Upscale Loft in the Historic District Cambridge, MD

The price is NZ$445
includes taxes & fees
29 Sept - 30 Sept
Station House East: Upscale Loft in the Historic District Cambridge, MD

Waterfront property with private boat ramp and new dock!

9.2 out of 10, Wonderful, (16)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

Thorneton Point Estate

9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
The price is NZ$479
includes taxes & fees
1 Oct - 2 Oct
Waterfront Getaway with Dock

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

10.0 out of 10, Exceptional, (90)
"This property is even prettier in person!! We have a huge extended family and there was plenty of space for everyone. The host and property manager both made themselves available to answer any questions and responded very quickly. Excellent trip - we would love to stay again in the future!"
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

10.0 out of 10, Exceptional, (10)
"Amazing "
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is NZ$510
includes taxes & fees
29 Sept - 30 Sept
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

9.4 out of 10, Exceptional, (3)
"Very beautiful property with clean rooms. Very responsive property management. Unfortunately the Outdoor grill and the dock light was not functional and the owner did bot resolve it during our stay. Hopefully they will take care of them before the next guest arrives."
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (47)
"Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. "
The price is NZ$768
includes taxes & fees
28 Sept - 29 Sept
Beautiful Waterfront Retreat in Cambridge!

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (38)
"We really enjoyed our stay. The house has everything needed and the sunrises are beautiful."
Stylish Home on the Choptank River (with Tidal Beach)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.4 out of 10, Exceptional, (20)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Minutes from Downtown Easton and St. Michaels | Pool

10.0 out of 10, Exceptional, (2)
"House was perfect for 5 adults and infant. Everyone had ample space but could come together. Property was spotless. Pool and dock were wonderful. Landscaping needs attention and it would have been nice to have a fire pit for the evenings. Otherwise a great place and space!!"
Minutes from Downtown Easton and St. Michaels | Pool

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
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

Find out more about Whitehall

Everything you need to know about Whitehall holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Whitehall holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Whitehall holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Whitehall holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Whitehall. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Whitehall holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Whitehall holiday rentals we have selected for you start as low as NZ$436 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Whitehall rentals

At Expedia, we put the best Whitehall holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Whitehall rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Whitehall holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Whitehall. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina: This holiday home rental outside of Whitehall is located in the city centre, and has a garden, a selection of games and air conditioning to put you at ease 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. Dorchester County Visitors Center and Choptank River Lighthouse 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.