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Top Holiday Rentals in Whitehall

Our top choices for Whitehall holiday rentals

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is £303
includes taxes & fees
22 Aug - 23 Aug
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

9.8 out of 10, Exceptional, (73)
"We had a wonderful stay including boating, kayaking, swimming, fishing, campfires and crabs! The house was perfect for our group and the owner was very accommodating."
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

10.0 out of 10, Exceptional, (9)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (43)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is £354
includes taxes & fees
3 Sept - 4 Sept
Beautiful Waterfront Retreat in Cambridge!

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"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!

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (132)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Casa Maria heart of downtown Cambridge Maryland

9.8 out of 10, Exceptional, (10)
"Place was quiet and clean. Few minutes drive from the center of town. Definitely a great experience!"
Casa Maria heart of downtown Cambridge Maryland

Amazing views waterfront 3-bedroom home in Madison

9.6 out of 10, Exceptional, (5)
Amazing views waterfront 3-bedroom home in Madison

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

9.6 out of 10, Exceptional, (31)
"Very roomy and lots of amenities. Superb location and private. Easy check-in and check-out. Guest contact was awesome - very responsive! Thanks so much!"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (48)
"wonderful home and great views. Clean, quiet, plenty of amenities"
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

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

8.6 out of 10, Excellent, (8)
"Spacious, orderly interior, lovely setting, great amenities: kayaks, fire pit, creek feeds into Chop tank, close to Saint Michaels and Secretary.Big bedrooms with new comfy beds, plenty of bathrooms and showers.Just a lovely place and excellent communication from host."
The price is £541
includes taxes & fees
25 Aug - 26 Aug
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"House was spacious plenty of room, great amenities, and very clean! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

9.4 out of 10, Exceptional, (8)
"Thank you for a beautiful stay! Well appointed kitchen, comfortable beds and a pristine lot. "
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Escape with family or friends to this peaceful, 4-bedroom retreat on the water

2.0 star property
10.0 out of 10, Exceptional, (7)
"House is clean, renovated, and comfortable. View was gorgeous. Hosts were helpful and timely in communications. Enthusiastically recommend. "
Escape with family or friends to this peaceful, 4-bedroom retreat on the water

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

10.0 out of 10, Exceptional, (9)
"This is such a special property. The house, the amenities and then the surprising foodie scene in Easton and St. Michael’s is within minutes. This is our second summer at this property and we are already starting to plan our third!"
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

10.0 out of 10, Exceptional, (4)
"Very relaxing house to stay in. Plenty of room and well stocked kitchen . Close to St. Michaels and Cambridge. We were there for the Eagleman triathlon and we really enjoyed the seclusion. "
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

Charming Waterfront Stay close to St. Michaels

9.8 out of 10, Exceptional, (12)
"Great house, updated, amazing views "
Charming Waterfront Stay close to St. Michaels

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home

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

9.8 out of 10, Exceptional, (6)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
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

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 Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW: This holiday home rental outside of Whitehall is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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. Bill Burton Fishing Pier State Park and Dorchester County Visitors Center 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.