West Annapolis holiday rentals

We found 61 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in West Annapolis that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as a fireplace and a washer and dryer. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – West Annapolis

Showing deals for:22 Jan - 29 Jan

Large, beautifully updated kitchen area is perfect for meal times.
Exceptional
(39 reviews)

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis

7% off
AU$9,190
for 7 nights, 1 home
AU$1,313 per night
includes taxes & fees
West Annapolis Cottage- 6BR Walk to Navy Stadium
Private kitchen
Exceptional
(12 reviews)

Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok

Annapolis

8% off
AU$10,265
for 7 nights, 1 home
AU$1,466 per night
includes taxes & fees
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
City Dock
Exceptional
(40 reviews)

Gem in Downtown Annapolis, close to USNA, St. John's College

Annapolis

8% off
AU$4,566
for 7 nights, 1 home
AU$652 per night
includes taxes & fees
Gem in Downtown Annapolis, close to USNA, St. John's College
Dining
Exceptional
(36 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis

8% off
AU$6,844
for 7 nights, 1 home
AU$978 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Exterior
Exceptional
(12 reviews)

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis

7% off
AU$4,044
for 7 nights, 1 home
AU$578 per night
includes taxes & fees
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Private kitchen
Exceptional
(131 reviews)

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Annapolis

12% off
AU$1,685
for 7 nights, 1 apartment
AU$241 per night
includes taxes & fees
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What are the top attractions in West Annapolis, Maryland, United States of America?
In West Annapolis, visitors can enjoy a charming blend of history and nature. The area is renowned for its proximity to the scenic Spa Creek, where you can take leisurely strolls along the waterfront and appreciate the beautiful views. The historic district nearby features quaint boutiques and cafés, great for a relaxing day out.Just a short distance away, the United States Naval Academy offers fascinating tours that delve into the history of naval traditions. The nearby Maryland State House, with its stunning architecture, is another must-see, providing insights into the state's legislative history.For those interested in outdoor activities, the nearby Broadneck Park offers sports fields and walking trails, ideal for families and nature enthusiasts alike.
Are all fees included in the West Annapolis holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any West Annapolis holiday homes with parking?
Stayz offers a wide selection of holiday homes in West Annapolis with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for West Annapolis holiday homes?
You can find great discounts on holiday homes in West Annapolis on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my West Annapolis holiday home booking on Stayz?
To find West Annapolis holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in West Annapolis?
A long-stay holiday home in West Annapolis is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a West Annapolis holiday home?
Book your West Annapolis holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in West Annapolis?
Prices for holiday homes in West Annapolis vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in West Annapolis to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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