Whitehall Holiday Rentals from €275: Search Short-Term Rentals

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

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock! : This holiday home rental outside of Whitehall is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

Check Whitehall holiday rental availability

Holiday Rentals in Whitehall

" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...

"Had a great visit. House was perfect and the area is absolutely gorgeous"

"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."

"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "

includes taxes & fees

25 Nov - 26 Nov

"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."

includes taxes & fees

30 Nov - 1 Dec

"This is a hidden jewel. We had so much fun fishing and crabbing. The home was everything you could ever ask for. We will definitely be back next year for a longer stay. If you are looking for some peace and quiet, this is the place to be. Thank you to the owners for making this a great place. "

"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."

"Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing. "

"We loved everything about this sweet cottage on the water! The decor was top notch, and so welcoming! We stayed 3 nights, and can’t say enough about this beautiful area of Maryland. Great restaurants, shoppes, and delicious crabs! We also did the ferry ride over to Oxford. Had an amazing time at this property! The host also left some yummy treats, and a bottle of champagne for our anniversary! Can’t wait to come back!"

"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."

"This house exceeded our expectations in every way. The kitchen is large and well-appointed, the beds are comfortable, and the peace and quiet is priceless. We enjoyed morning coffee in the sunroom, table tennis in the crab house, sunsets from the dock, and stargazing at the firepit. If you desire peace and quiet this house is a perfect choice!"

includes taxes & fees

1 Dec - 2 Dec

"We stayed at Saddle House during 2024 Ironman Maryland, with 2 Ironmans competing and lots of support traveling to stay. I was concerned choosing a house about 20 minutes from the start/finish but it was an amazing choice with great bike route access. House is secluded and serene, amazing cleanliness, kitchen with everything you could ever need. Pictures are very accurate to the product you get. Jon was a great help finding things to do, house has incredible resources that support you during...

"The original home is unique and gorgeous and the additions, the sunroom facing sunrises and the lodge style master chef kitchen gave us plenty of room to spread out. The large lawn and driveway gave us plenty of areas to walk the dogs and the beach was a daily swim spot for the dogs. The pool was one of the nicest we have had yet. We love the places with nice pools facing the boats out on the water. We will be back again for sure"

"We had a wonderful stay here. The house has a really functional kitchen so we were able to cook a lot of meals here. The pool was perfect for young swimmers (decent sized shallow end) and we loved hanging out on the dock, crabbing and kayaking. With plenty of adult bikes, we took a trip each morning to the playground too. We hope to be back!"

"Wonderful home for our girl's weekend getaway. Beautiful property on the water and close to Easton and St Michael's"

"Excellent property ! Had everything we needed and wanted and more. Waterfront views and shorebirds beautiful ! We hope to revisit !!! "

"Our 2nd stay at staying at Loon Cottage. The property, water views, house, dock etc…all amazing! 15mins from St Michaels, 10mins from grocery/shopping. Owners are amazing! Very accommodating if you need anything. 10/10 recommend! "

"This stay was perfect. The location was charming and safe, and the home was clean and cozy. Jennifer was a very accommodating and responsive host."

includes taxes & fees

16 Dec - 17 Dec

"The property owner was a pleasure to work with. The view is stunning and the house had everything we needed and more. The home is located in a beautiful area and was a quick drive to downtown. Sunrise and sunset over the water was absolutely beautiful. "

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Other types of properties in Whitehall you may be interested in

Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers

"Best vacation ever!"

includes taxes & fees

2 Dec - 3 Dec

"This property is not fancy but it is a very good value. Rooms could use a little face lift but everything is clean, functional and useable. Mattress was excellent; TV only 24 inches but OK. Breakfast was fine. "

includes taxes & fees

8 Dec - 9 Dec

Premium bedding, desk, iron/ironing board, free cots/infant beds

"easy location"

includes taxes & fees

24 Nov - 25 Nov

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, apart-hotels, 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 €275 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.

Recent reviews of Whitehall properties

5/5 Excellent

"Check in for this hotel is 4 pm. We arrived around 11:30 am to park the car, have lunch and see some of the town. Stopped at the front desk and they actually checked us in early!!! Room was small but clean. No fridge, and the heat is controlled by a central unit somewhere not by the thermostat in the room. Got a little chilly overnight and found that the temp was 66! "

A verified traveller stayed at The Tidewater Inn

Posted 5 days ago

5/5 Excellent

"We really enjoyed our stay at the Sandaway. It was quiet and peaceful in a wonderful spot, right on the water, next to the yacht club. We loved walking around Oxford, a quaint and historic little town. A quick strolling over to the Market for breakfast sandwiches and the Social Cafe for great espresso based coffees and pastries. Contactless check-in was a breeze. Having prepaid, we found our designated parking spot, went to our room and our key was in the lock. Complimentary water bottles and goodies thoughtfully welcomed us. Our “room” turned out to be a suite with full kitchen, sitting area and two TVs. The feel of the place, the bathroom etc, is pretty rustic and dated, but that didn’t bother us at all. It felt appropriate to the feel of the lovely town. "

A verified traveller stayed at Sandaway Suites & Beach

Posted 12 days ago

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?

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!: This holiday home rental outside of Whitehall is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Whitehall?

Explore the area and family-friendly sights such as Bay Country Shop, 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.

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Holiday Rentals in Whitehall

Check Whitehall holiday rental availability

Holiday Rentals in Whitehall

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Eastern Shore Waterside Cottage Near St. Michaels

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Waterfront Getaway with Dock

Cottage on Cabin Creek

Bay Views & Fire Pit: Taylor’s Island Retreat

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Cottage at Goose Neck Point

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

Beautiful Waterfront Retreat in Cambridge!

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

Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach

Breathtaking Waterfront Estate

Modern St. Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks & More

St. Michaels Waterfront Home

Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Other types of properties in Whitehall you may be interested in

Hyatt Regency Chesapeake Bay

St Michaels Inn

Days Inn & Suites by Wyndham Cambridge

Find out more about Whitehall

Recent reviews of Whitehall properties

The Tidewater Inn

Comfort Inn & Suites Cambridge

St Michaels Inn

Best Western Plus Easton Inn & Suites

Holiday Inn Express Cambridge, an IHG Hotel

Fairfield Inn & Suites by Marriott Easton

Days Inn & Suites by Wyndham Cambridge

Sandaway Suites & Beach

Hyatt Regency Chesapeake Bay

Frequently asked questions