Whitehall Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Whitehall holiday rentals

A wooden interior with a dining area, sofas, and a table.

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

Cambridge

Anonymous traveller

HK$5,190 total

includes taxes & fees

25 Aug - 26 Aug

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

2. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

HK$1,995 total

includes taxes & fees

25 Aug - 26 Aug

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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

Downtown Cambridge

Sylvie G.

HK$4,039 total

includes taxes & fees

22 Sept - 23 Sept

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

Downtown Cambridge

Kristen S.

HK$3,889 total

includes taxes & fees

22 Sept - 23 Sept

A marina with boats docked, a water tower, and residential buildings with balconies.

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

Cambridge

Melissa

HK$3,094 total

includes taxes & fees

21 Sept - 22 Sept

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

Cambridge

Robert

HK$3,939 total

includes taxes & fees

22 Sept - 23 Sept

A bedroom with a bed, pillows, a bookshelf, and a window with curtains.

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

Downtown Cambridge

HK$1,978 total

includes taxes & fees

25 Aug - 26 Aug

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

8. Waterfront Getaway with Dock

Woolford

Meagan G.

HK$2,186 total

includes taxes & fees

23 Aug - 24 Aug

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Top Whitehall Hotel Reviews

Best Western Plus Easton Inn & Suites

10/10 Excellent

"Great hotel. Staff was very friendly and helpful. They provided good recommendations for restaurants. Fair price."

Hyatt Regency Chesapeake Bay

10/10 Excellent

"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future."

Hummingbird Inn

10/10 Excellent

"We had a fantastic stay at Hummingbird Inn. It is a lovely old house with so much charm . Eric was a great host, we had a lovely evening chat on the front porch, and in the morning we sneaked out early with our dog for a walk and sat later with a morning coffee on the lovely porch waiting for our son to wake up, just relaxing before breakfast. The breakfast and breakfast room was such a treat, you must try the Hummingbird Bellini, everything was delicious. We can only highly recommend Hummingbird inn, so beautiful, relaxing, welcoming, and petfriendly!"

Private 2 Acre Waterfront Family Retreat with Pool & Pier

10/10 Excellent

"Wonderful home with plenty of space. Large bedrooms made it easy to accommodate our family of 19. We had a few hiccups with pool and air conditioning but Ginger was super responsive and very helpful in getting everything fixed as quickly as possible. The dock was great. The pool was a nice feature for our family. Everything is a bit worn and I think a deep cleaning would be helpful, (especially the high up areas where dust accumulates) but we will stay here again!"

The Oaks Waterfront

10/10 Excellent

"The Oaks Waterfront was exactly the kind of getaway we were looking for. Tucked away in a quiet, secluded setting, it feels like you’re escaping from everything, yet St. Michaels is only a short ride away thanks to their beautiful shuttle. It really gives you the best of both worlds. What stood out most to us was the family-owned and operated feel. Everyone was genuinely friendly, and there was a warmth about the property that made it feel less like a hotel and more like staying with incredibly hospitable friends. It has a relaxed, welcoming atmosphere that makes it easy to settle in. We stayed in one of the cottages, and it was beautifully appointed with comfortable bedding and thoughtful touches that made it feel luxurious without trying too hard. The entire property is impeccably maintained, and you can tell the owners take great pride in every detail. We also traveled with our two dogs, and they were just as welcome as we were. They loved the cottage, and we appreciated the dog beds, bowls, and bottled water waiting for them. Those little touches made all the difference. The food was fresh and delicious, and the complimentary breakfast each morning was another example of the attention to detail they put into the guest experience. A special thank you to Kathie, Brad, Linda, and the entire team, including housekeeping. Their kindness and genuine hospitality are what make The Oaks such a special place."

Find out more about Whitehall

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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.

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Treat yourself

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Check prices for these dates

Our top choices for Whitehall holiday rentals

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

2. Sailwinds Loft at Cambridge Creek

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

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

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

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

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

8. Waterfront Getaway with Dock

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

10. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

11. Sunset Breezes - quiet waterfront retreat

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

Find holiday rentals that suit your style

Top Whitehall Hotel Reviews

Best Western Plus Easton Inn & Suites

Sandaway Suites & Beach

Hyatt Regency Chesapeake Bay

Hampton Inn Easton

Holiday Inn Express Cambridge by IHG

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

Hummingbird Inn

Private 2 Acre Waterfront Family Retreat with Pool & Pier

The Oaks Waterfront

Find out more about Whitehall

Frequently asked questions

Go further with the Expedia app

Whitehall Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Whitehall holiday rentals

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

2. Sailwinds Loft at Cambridge Creek

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

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

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

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

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

8. Waterfront Getaway with Dock

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

10. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

11. Sunset Breezes - quiet waterfront retreat

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

Find holiday rentals that suit your style

Top Whitehall Hotel Reviews

Best Western Plus Easton Inn & Suites

Find out more about Whitehall

Frequently asked questions

Go further with the Expedia app

10. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8