Vacation rentals in Deale

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Top-rated vacation rentals in Deale

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Guest favorite

Apartment in North Beach

4.97 out of 5 average rating, 102 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

Mar 3 – 10

$113 per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Dec 25 – Jan 1

$85 per night

Guest favorite

Cottage in North Beach

4.95 out of 5 average rating, 124 reviews

Club Carp North Beach - Steps to the Bay!

Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with three bedrooms and two full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced yard with a swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars. (We are at Dayton and 7th st).

May 7 – 14

$190 per night

Guest favorite

Guesthouse in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Jul 30 – Aug 6

$156 per night

Guest favorite

Guest suite in Upper Marlboro

4.95 out of 5 average rating, 104 reviews

Private Apartment on a Horse Farm

My place is convenient to Joint Base Andrews (20 minutes), Washington DC and Annapolis MD (both are about 40 minutes by car) but you’ll love my place because of the outdoor space and the peace and quiet. For Equestrians, we are within 10 minutes of the Prince George's Equestrian Center as well. My place is good for couples, solo adventurers, families (with kids), and well-behaved pets. With a full-sized kitchen, this apartment is a great home away from home.

Jun 28 – Jul 5

$85 per night

Guest favorite

Home in Deale

4.98 out of 5 average rating, 113 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Bring your own boat! Make wonderful memories. Great place for families and multi family groups.

Aug 18 – 25

$469 per night

Guest favorite

Apartment in Deale

4.91 out of 5 average rating, 614 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Jan 6 – 13

$189 per night

Guest favorite

Home in Deale

4.99 out of 5 average rating, 125 reviews

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

Nov 5 – 12

$204 per night

Guest favorite

Cottage in Deale

4.95 out of 5 average rating, 138 reviews

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes private little pier, sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Three bedroom. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

Nov 13 – 20

$247 per night

Guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 165 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower.

Nov 11 – 18

$400 per night

Guest favorite

Cottage in North Beach

4.96 out of 5 average rating, 269 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

May 6 – 13

$165 per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.

Aug 29 – Sep 5

$108 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Deale vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Deale's top sights

Skipper's Pier Restaurant & Dock Bar48 locals recommend

Happy Harbor Restaurant30 locals recommend

Dockside Restaurant & Sports Bar25 locals recommend

South County Cafe30 locals recommend

JesseJay's Latin Inspired Kitchen16 locals recommend

Deale Umai Sushi House19 locals recommend

Other great vacation rentals in Deale

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 116 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Sep 20 – 27

$380 per night

Guest favorite

Home in Shady Side

4.97 out of 5 average rating, 64 reviews

Canary Pointe-A popular getaway for 2!

Dec 28 – Jan 4

$147 per night

Guest favorite

Home in Deale

5.0 out of 5 average rating, 7 reviews

Quiet Getaway in Waterfront Community

May 2 – 9

$186 per night

Guest favorite

Cottage in North Beach

4.95 out of 5 average rating, 77 reviews

Quiet Coastal Cottage Escape with Water Views

Dec 21 – 28

$138 per night

Guest favorite

Home in Deale

4.99 out of 5 average rating, 80 reviews

8 Acre Pet-Friendly, Waterfront Oasis ! 140ft Pier

Apr 26 – May 3

$225 per night

Guest favorite

Cottage in Deale

4.98 out of 5 average rating, 64 reviews

Private Water View Home | Near Watersports & Fun!

Oct 18 – 25

$282 per night

Guest favorite

Home in Deale

5.0 out of 5 average rating, 5 reviews

Private Waterfront Home 2+ Acres

Jan 19 – 26

$351 per night

Guest favorite

Guest suite in Chesapeake Beach

4.95 out of 5 average rating, 82 reviews

Nice Guest Suite at Chesapeake Bay

Sep 8 – 15

$122 per night

Show all

Quick stats about vacation rentals in Deale

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.6K reviews
Nightly prices starting at
$90 before taxes and fees

Frequently Asked Questions

Do house rentals in Deale have free parking?
Absolutely! We offer over 20 house rentals with free parking in Deale. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Deale?
Experience the best of Deale with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Deale have wifi?
Absolutely! We offer over 20 house rentals with wifi in Deale. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Deale?
Four-legged friends are welcome in Deale. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Deale have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Deale. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Deale?
Deale has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Deale?
Yes! Work meets play with ease at over 20 vacation rentals in Deale featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Deale?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Deale

Top-rated vacation rentals in Deale

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Deale vacation rentals

Stay near Deale's top sights

Other great vacation rentals in Deale

Home in Shady Side

Home in Shady Side

Home in Deale

Cottage in North Beach

Home in Deale

Cottage in Deale

Home in Deale

Guest suite in Chesapeake Beach

Quick stats about vacation rentals in Deale

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Deale have free parking?

How much does it cost to stay in house rentals in Deale?

Do house rentals in Deale have wifi?

Are there pet-friendly vacation rentals in Deale?

Do house rentals in Deale have air conditioning?

Are there family-friendly vacation rentals in Deale?

Are there vacation rentals with a dedicated workspace in Deale?

What are the most popular amenities for House Rentals in Deale?

Destinations to explore