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Annapolis Vacation Rentals & Ski-in/Ski-out Homes

About Annapolis Vacation Rentals

Explore over 1248 vacation rentals in Annapolis with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Annapolis for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Annapolis. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Annapolis tailored to your preferences. On average, these rentals offer 983.27 ft² of space, and are priced at an average of US $561 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Annapolis at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Annapolis

Type Count
Vacation Homes 882
Holiday Apartments 127
Cottages 33
Unique Vacation Rentals 22
Villas 6
B&B 5
Cabin Rentals 2
Others 1
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Annapolis

★ Pro Tip: Discover Your Ideal Vacation Rental in Annapolis with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in Annapolis, MD

View the weather forecast for Annapolis before booking your Annapolis Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Annapolis, MD

Sunski offers a large selection of top attractions around Annapolis . Research things to do on your vacation before you visit Annapolis.


U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Bowie State University
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
Annapolis Maritime Museum
Allen Pond Park
Maryland Quiet Waters Park
St John's College
Bay Hills Golf Club
Maryland World War II Memorial
William Paca House
The Kunta Kinte Alex Haley Memorial

Other Places to Stay in Annapolis, MD


Northern Chesapeake Bay 12,155 Properties
Historic District 448 Properties
Kent Island 88 Properties
Parole 83 Properties
Bowie 81 Properties
Stevensville 71 Properties
Eastport 65 Properties
Edgewater 52 Properties
Selby-on-the-Bay 42 Properties
Lake Arbor 32 Properties
Cape Saint Claire 26 Properties
Arnold 26 Properties

Complexes around Annapolis, MD


Prince George St Annapolis 7 Properties
Comfort Inn Conference Bowie 3 Properties
Courtyard 3 Properties
Doubletree 3 Properties
Hampton Inn Bowie 3 Properties
Stay America Suites Washington Landover 3 Properties
Eastport 2 Properties
The Inn At Chesapeake Bay Beach Club 2 Properties

Frequently Asked Questions About Annapolis?

What are the top vacation rentals in Annapolis?

When organizing your trip to Annapolis, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Annapolis. Peruse our collection of highly-rated properties and secure your reservation today.

How many vacation rentals have private pools in Annapolis?

Uncover 61 vacation rentals boasting private pools near Annapolis. Explore top-rated RBO homes offering access to a swimming pool:

Which vacation homes or resorts in Annapolis are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Annapolis. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Annapolis?

Discover the ideal vacation rental in Annapolis with SunSki Resorts™. We provide an extensive selection of over 1248 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Annapolis.

Nearby Neighborhood (16) 
Neighborhood Property Count
Historic District Vacation Rentals in Annapolis, Maryland 448
Eastport Vacation Rentals in Annapolis, Maryland 65
Murray Hill Vacation Rentals in Annapolis, Maryland 24
Hillsmere Vacation Rentals in Annapolis, Maryland 718
West Annapolis Vacation Rentals in Annapolis, Maryland 710
Arundel on the Bay Vacation Rentals in Annapolis, Maryland 155
Homewood Vacation Rentals in Annapolis, Maryland 722
Epping Forest Vacation Rentals in Annapolis, Maryland 329
Oyster Harbor Vacation Rentals in Annapolis, Maryland 220
Atlantis Vacation Rentals in Annapolis, Maryland 89
Cape St. John Vacation Rentals in Annapolis, Maryland 176
Anchorage Vacation Rentals in Annapolis, Maryland 631
Hunt Meadows Vacation Rentals in Annapolis, Maryland 776
Kingsport Vacation Rentals in Annapolis, Maryland 737
Winchester-on-the-Severn Vacation Rentals in Annapolis, Maryland 505
Downs on the Severn Vacation Rentals in Annapolis, Maryland 149

People Also Ask

There are 1248 Annapolis, MD Vacation Rentals

Recently Booked Vacation Rentals in Annapolis