Deale Vacation Rentals

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Nov 24 - Nov 25
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Dec 5 - Dec 7

Vacation Rentals in Deale

Dining
Million Dollar View of the Chesapeake Bay

Vacation Home in Deale

9.8 out of 10, Exceptional, (130)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Vacation Home in Historic District

10.0 out of 10, Exceptional, (33)
"Our stay was AMAZING! Perfect location, plenty of space! Will definitely book again when we have a larger group like we did for PPW! "
United States
Charolene P.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Vacation Home in Stevensville

10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Cabin in Port Republic

10.0 out of 10, Exceptional, (180)
"Everything about this cabin was just what we were looking for! From the initial booking until we left we were taken care of by Brett. The pictures on-line were spot on but seeing the bay view in person from the windows and deck took my breath. There was a lot to do and we took advantage of close by activities (hiking, paddle-boarding, kayaking, jet skiing) but the cabin is a destination in itself with it's peaceful and calm surroundings. We were blessed with beautiful sunrises, hummingbirds and...
United States
Vicki K.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Exterior
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Vacation Home in Historic District

10.0 out of 10, Exceptional, (124)
"This house is in a wonderful location relative to town and the Naval Academy. The house is lovely and was very comfortable for all 6 of us. Clean, spacious, and great bedding. The garden is beautiful. Arranging for parking on the street was great."
United States
cara
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Vacation Home in Historic District

9.4 out of 10, Exceptional, (18)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
United States
Kerry G.
$1,019 nightly
The price is $1,161
Dec 2 - Dec 3
Total with taxes and fees
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (39)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Mobile Home in Edgewater

10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
Waterfront Getaway, Dock Your Boat & Play!
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in Arnold

9.4 out of 10, Exceptional, (33)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
$287 nightly
The price is $327
Nov 25 - Nov 26
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Vacation Home in Tracys Landing

9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Cottage in St Michaels

9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Vacation Home in Edgewater

9.8 out of 10, Exceptional, (24)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
$570 nightly
The price is $613
Dec 9 - Dec 10
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
Outdoor dining
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Vacation Home in Annapolis

7.0 out of 10, Good, (6)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
United States
Kristin W.
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Smart TV, fireplace, books, offices
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Vacation Home in Port Republic

10.0 out of 10, Exceptional, (124)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Apartment in Annapolis

9.4 out of 10, Exceptional, (34)
"Very communicative host and the in apartment sauna and jacuzzi tub really helped us relax. A great stay overall!"
United States
George H.
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Vacation Home in St. Michaels

9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Apartment in Saint Michaels

10.0 out of 10, Exceptional, (54)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Property grounds
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Vacation Home in Crofton

9.6 out of 10, Exceptional, (99)
"Food options where very good, there was more than enough options to choose from (which we loved). "
United States
Marcus
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Vacation Home in Sherwood

10.0 out of 10, Exceptional, (20)
"Fantastic property"
United States
Harvey W.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
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 Deale Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Staff was friendly, food was good. Roo. Was clean and comfy."
Rebecca 1-night trip
Posted 16 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Deale

Everything you need to know about Deale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Deale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Deale vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Deale vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $327 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Deale rentals

At Expedia, we put the best Deale vacation 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 Deale 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 Deale vacation.

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

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Deale?

Yes, we give you a choice of vacation rentals near the most popular sights in Deale, or you can go with a more remote option if you want a relaxing place to stay. Deale is known for its waterfront and bars. Make sure you have time to check out the shopping and live music during your trip.

What are some of the best vacation rentals in Deale?

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!: This vacation home rental near Deale is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Deale?

Choose from 6 Expedia vacation rentals in Deale for a memorable vacation.

What’s there to see and do in Deale?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Shadyside Park and Chesapeake Beach Water Park.

What’s a vacation rental in Deale like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Deale. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.