Sombrero Beach Vacation Homes - Vacation Rentals in West Annapolis

All Star Annapolis Retreat - Walk To Stadium From US $589
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
PERFECT LOCATION in the heart of history From US $518
         

10.0 (223 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Flag House Inn From US $255
         

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9.2 (89 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Nautical Feel to This Beautiful Eastport Home From US $705
         

9.8 (59 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Your Annapolis Adventure Starts Here! From US $616
         

10.0 (148 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in West Annapolis

Over 808+ Luxury Places to Stay in or Near West Annapolis
Waterfront mid-century home From US $2,109
         

New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Lighthouse Inn From US $1,726
         

New
House
  • Barbecue/Outdoor Cooking
  • Child Friendly

Top-Rated Vacation Rentals with a Pool in West Annapolis

Over 67+ Top-Rated Vacation Rentals with a Pool in or Near West Annapolis
Annapolis Entertainment Complex From US $743
         

10.0 (95 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Oasis of Annapolis Star From US $461
         

10.0 (81 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Prime Eastport Location - Waterfront Condo with Parking From US $504
         

Annapolis Garden Suite From US $277
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront 2-Bedroom Condo on Spa Creek From US $516
         

10.0 (11 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in West Annapolis

Over 214+ Pet-Friendly Vacation Rentals in or Near West Annapolis
Historic Row Home 1 Block from Gate 1 at USNA From US $538
         

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9.6 (5 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • View
Eastport Historic Firehouse with Parking, Dogs OK From US $671
         

10.0 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Red Roof Inn Annapolis From US $84
         

7.2 (442 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
New Downtown Annapolis Condo With Free Parking From US $369
         

10.0 (39 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
USNA Home Steps to Stadium Dog-Friendly w Parking From US $844
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in West Annapolis

Over 157+ Large Vacation Homes & Villas in or Near West Annapolis
Gaia House From US $126
         

9.3 (59 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Annapolis Victorian From US $884
         

10.0 (73 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
USNA Luxury Home, parking, pet friendly From US $910
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in West Annapolis

Over 94+ Wheelchair Accessible Vacation Homes in or Near West Annapolis
1313 West Luxury Boutique Hotel From US $311
         

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10.0 (1 Review)
Hotel
  • Air Conditioner
  • Parking
  • TV
Upscale Condo in Annapolis w/Private Parking From US $564
         

86 State Circle - Luxury Boutique Hotel From US $329
         

10.0 (4 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Beautiful Condo - Water View Near City Dock From US $239
         

9.6 (162 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

West Annapolis Vacation Rentals and Airbnb Places to Stay Under $200

Over 81+ West Annapolis Vacation Rentals and Airbnb Places to Stay Under $200
Inn on Main Annapolis From US $129
         

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8.3 (316 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! From US $144
         

Candlewood Suites Annapolis by IHG From US $126
         

9.0 (258 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Annapolis waterfront "tiny house" in garden setting From US $171
         

Extended-Stay Annapolis Home Near USNA & Downtown From US $200
         

9.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in West Annapolis

Over 403+ Instantly Bookable Vacation Homes in or Near West Annapolis
Cozy 2br home w/parking in downtown Annapolis From US $450
         

Bay View Studio Apartment From US $319
         

10.0 (62 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Eastport Cottage .5 mi from Downtown Annapolisnn From US $448
         

About West Annapolis Vacation Rentals

With more than 817 West Annapolis vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Sombrerobeachvacationhomes and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in West Annapolis.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sombrerobeachvacationhomes West Annapolis, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in West Annapolis. Places to stay near West Annapolis are 907.55 ft² on average, with prices averaging US $593 a night.

Sombrerobeachvacationhomes makes it easy and safe to find and compare vacation rentals in West Annapolis with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in West Annapolis

Type Count
Vacation Homes 556
Hotels 92
Holiday Apartments 89
Cottages 16
Villas 4
B&B 3

Use these Quick Filters to Find a Vacation Rental in West Annapolis

Pro Tip: Sombrerobeachvacationhomes makes it easy to compare the best listings on Sombrerobeachvacationhomes homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sombrerobeachvacationhomes homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in West Annapolis.

Weather in West Annapolis

View the weather forecast for West Annapolis before booking your West 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

Other Places to Stay Near West Annapolis, MD


West Annapolis Vacation Rental Frequently Asked Questions

What are the top vacation rentals in West Annapolis?
How many vacation rentals are available in West Annapolis?

Currently, the total number of properties listed in 2026 is over 817 in the West Annapolis area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in West Annapolis.