Vacation rentals in Deale

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Top-rated vacation rentals in Deale

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Sep 11 – 18

R8,283 ZAR per night
Guest favorite

Apartment in North Beach

4.97 out of 5 average rating, 100 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 14 – 21

R2,476 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 202 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 1 – 8

R1,856 ZAR per night

Popular amenities for Deale vacation rentals

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

Cottage in Annapolis

4.94 out of 5 average rating, 308 reviews

Wright’s Cottage, Pets Welcome!

Aug 20 – 27

R3,521 ZAR per night
Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 112 reviews

Black Walnut Cove Retreat, Tilghman Island

Apr 6 – 13

R2,801 ZAR per night
Guest favorite

Guesthouse in Riva

4.99 out of 5 average rating, 273 reviews

The Riva House

Dec 4 – 11

R2,847 ZAR per night
Guest favorite

Home in North Beach

4.86 out of 5 average rating, 58 reviews

Light of North Beach

Jul 15 – 22

R1,879 ZAR per night
Guest favorite

Home in Shady Side

4.97 out of 5 average rating, 64 reviews

Canary Pointe-A popular getaway for 2!

Nov 16 – 23

R3,260 ZAR per night
Guest favorite

Cottage in North Beach

4.95 out of 5 average rating, 75 reviews

Quiet Coastal Cottage Escape with Water Views

Mar 19 – 26

R2,896 ZAR per night
Guest favorite

Home in Deale

4.99 out of 5 average rating, 78 reviews

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

Nov 30 – Dec 7

R6,537 ZAR per night
Guest favorite

Home in Deale

5.0 out of 5 average rating, 7 reviews

Quiet Getaway in Waterfront Community

Apr 24 – May 1

R4,076 ZAR per night
Guest favorite

Home in Deale

4.93 out of 5 average rating, 61 reviews

Million Dollar View

Jan 1 – 8

R5,092 ZAR per night
Guest favorite

Cottage in Deale

4.98 out of 5 average rating, 64 reviews

Private Water View Home | Near Watersports & Fun!

Aug 10 – 17

R5,323 ZAR per night
Guest favorite

Home in Deale

5.0 out of 5 average rating, 10 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Oct 24 – 31

R10,625 ZAR per night
Guest favorite

Guest suite in Chesapeake Beach

4.95 out of 5 average rating, 80 reviews

Nice Guest Suite at Chesapeake Bay

Dec 4 – 11

R2,652 ZAR per night

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

30 properties are a good fit for families

Total number of reviews

2.6K reviews

Nightly prices starting at

R1,517 ZAR 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 $80 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 30 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 free parking, over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Anne Arundel County
  5. Deale